Thiazolyl substituted aminopyrimidines as plant protection agents

ABSTRACT

Compounds of formula (I), or a salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are specified organic redicals; and compositions containing them, processes for making them and their use as fungicides.

The present invention relates to novelN-[4-(2-amino-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine derivatives,to a method of protecting plants against attack or infestation byphytopathogenic organisms, such as nematodes or insects or especiallymicroorganisms, preferably fungi, bacteria and viruses, or combinationsof two or more of these organisms, by applying anN-[4-(2-amino-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine derivative asspecified hereinafter to a part and/or to the site of a plant, to theuse of said derivative for protecting plants against said organisms, andto compositions comprising said derivative as the active component. Theinvention further relates to the preparation of these novelN-[4-(2-amino-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine derivatives.

Certain N-phenyl-N-(4-thiazolyl-pyrimidin-2-yl)-amine derivatives havebeen described in the art, e.g. in the PCT patent applications WO97/19065, WO 01/29009 and WO 01/30778, as having pharmacologicalproperties, mainly as tumor-inhibiting anti-cancer substances.

Surprisingly, it has now been found that the newN-[4-(2-amino-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine derivativesaccording to the present invention are effective in plant protectionshowing advantageous properties in the treatment of plant diseasescaused by phytopathogenic microorganisms. Further the fungicidalactivity allows to employ the compounds according to present inventionfor controlling fungi in related areas, e.g. in protection of technicalmaterials, including wood and wood related technical products, in foodstorage, in hygiene management, etc..

The novel N-[4-(2-amino-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-aminederivatives according to the invention are those of the formula I

whereinR₁ is hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₃-C₇cycloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl, C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl,C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, aryl-C₁-C₄alkyl, heteroaryl-C₁-C₄alkyl,or a group —CO—R₉, —CO—OR₁₀, —CO—NR₁₀R₁₁, or —NR₁₀R₁₁;R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl,C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl or agroup —CO—R₉;R₁ and R₂ together with the nitrogen to which they are bound form anoptionally substituted N-linked saturated or unsaturated N-ring systemwhich may contain oxygen or sulfur as a ring member, or form a group—N═CR₉—NR₁₀R₁₁;R₃ is hydrogen, halogen or C₁-C₄alkyl;R₄ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆cyanoalkyl,C₃-C₇cycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,C₂-C₆haloalkynyl, amino, C₁-C₆alkylamino, di(C₁-C₄alkyl)-amino, halogen,hydroxy, mercapto, cyano, C₁-C₆alkoxy, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy,C₁-C₆haloalkoxy, C₁-C₈alkanoyloxy-C₁-C₆alkyl, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆hydroxyalkyl,C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, C₁-C₈alkoxycarbonyl,C₁-C₈alkanoyl-C₁-C₆aminoalkyl, optionally substituted heterocyclyl,optionally substituted aryl, optionally substituted heteroaryl, or agroup —CO—R₉, —O—CO—R₉, —NH—CO—R₉, —(C₁-C₆alkylene-)-CO—R₉,—C(—O—C₁-C₆alkylene-O—)—R₉, —C(═NOR₈)—R₉ or —CO—NR₁₀R₁₁;R₅ is hydrogen, hydroxy, halogen, C₁-C₆alkyl, C₁-C₆alkoxy orC₁-C₆haloalkyl;R₆ is hydrogen, C₁-C₆alkyl or C₁-C₆haloalkyl;R₇ is thienyl , pyridinyl or aryl each optionally substituted with oneto three substituents independently selected from the group comprisinghalogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy;R₈ is hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₁-C₄alkoxy-C₁-C₆alkyl, or a group —CO—R₉ or —CO—OR₁₀;R₉ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₇cycloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl, aryl, C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl,aryl-C₁-C₄alkyl, heteroaryl or heteroaryl-C₁-C₄alkyl;R₁₀ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl orC₁-C₄alkoxy-C₁-C₆alkyl;R₁₁ is C₁-C₆alkyl, C₃-C₇cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl,C₁-C₄alkoxy-C₁-C₆alkyl, aryl or heteroaryl ; or a salt thereof.

The symbols and generic expressions used above are defined as below.Where radicals are combined from other sub-radicals, the definition ofresulting new radical likewise follows from the combination of thedefinitions of said sub-radicals.

In this document “halogen” or the prefix “halo” shall include fluorine,chlorine, bromine and iodine. Preferably, this definition designatessubstitution with fluorine or chlorine.

Alkyl—as a group per se and as a structural element of hydroxyalkyl,aminoalkyl, dialkylamino, cycloalkylalkyl, alkoxy, alkoxyalkyl,alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenylyoxy,alkynyloxy, alkylene, alkanoyl, alkanoyloxy, alkanoylamino, arylalkyl,heteroarylalkyl, haloalkyl or haloalkoxy—is preferably C₁-C₆alkyl, morepreferably C₁-C₄alkyl. The alkyl, alkenyl and alkynyl radicals may bestraight-chain or branched. This applies also to the alkyl, alkenyl oralkynyl parts of other alkyl-, alkenyl- or alkynyl-containing groups.Depending upon the number of carbon atoms mentioned, alkyl on its own oras part of another substituent is to be understood as being, forexample, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl andthe isomers thereof, for example isopropyl, isobutyl, tert-butyl orsec-butyl, isopentyl or tert-pentyl. In many cases the short chain alkylgroups methyl or ethyl are preferred.

Alkoxy includes methoxy, ethoxy, propyloxy, isopropyloxy, butoxy,isobutyloxy, sec-butyloxy, tert-butyloxy, and the diverse pentyloxy andhexyloxy.

Depending upon the number of carbon atoms mentioned, alkenyl as a groupor as a structural element of other groups is to be understood as being,for example, ethenyl, allyl, 1-propen-1-yl, 2-propen-1-yl,1-propen-3-yl, 1-buten-2-yl, 1-buten-3-yl, 1-penten-1-yl, 2-penten-1-yl,1-penten-3-yl, hexen-1-yl, 4-methyl-3-pentenyl or 4-methyl-3-hexenyl.Optionally substituted alkenyl groups carry one to four, preferably notmore than two further substituents selected from the group halogen,C₁-C₄alkoxy, C₁-C₄alkylthio, phenyl, halophenyl, C₁-C₄alkylphenyl,benzyl, halobenzyl and C₁-C₄alkylbenzyl. Examples are stryryl,chloroallyl, dichloroallyl, trichlorovinyl, 4,4,4-trifluoro-2-butenyl.

Alkynyl as a group or as a structural element of other groups is forexample, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl,1-methyl-2-butynyl, hexyn-1-yl, 1-ethyl-2-butynyl or octyn-1-yl.Optionally substituted alkynyl groups carry one to four, preferably notmore than two further substituents selected from the group halogen,C₁-C₄alkoxy, C₁-C₄alkylthio, phenyl, halophenyl, C₁-C₄alkylphenyl,amino, C₁-C₄alkylamino, di-(C₁-C₄alkyl)-amino, benzyl, halobenzyl andC₁-C₄alkylbenzyl. Examples are phenylethinyl, phenylpropargyl,chloropropargyl or 5,5,5-trifluoro-2-pentinyl.

Alkenyloxy and alkynyloxy have analogous designations, employing theexemplified alkenyl and alkynyl radicals.

Alkylene designates a bivalent bridge member, being linked at both endsof the hydrocarbon chain, which may be straight or branched. Typicalexamples are methylene, 1,2-ethylene, 1-methyl-1,2-ethylene,1,2-dimethyl-1,2-ethylene, 1,1-dimethyl-1,2-ethylene,1-ethyl-1,2-ethylene, 1-propyl-1,2-ethylene, 1-butyl-1,2-ethylene,1,3-propylene, etc.. Where alkylene is attached to two oxygen atoms atboth ends, and both oxygen atoms are in turn bound to the same carbonatom as in the definition of R₄, then the functional group is that of aketal.

Cycloalkyl is, depending upon the number of carbon atoms mentioned,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclopentyl,bicyclohexyl or cycloheptyl. Likewise, cycloalkyl-alkyl oralkyl-cycloalkyl-alkyl encompass cyclopropylmethyl, cyclopropylethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopentylethyl, cyclohexylethyl,methyl-cyclopropylmethyl, methyl-cyclopropylethyl,dimethyl-cyclopropylmethyl, dimethyl-cyclopropylethyl,methyl-cyclopentylmethyl, methyl-cyclohexylmethyl,methyl-cyclopentylethyl, methyl-cyclohexylethyl,ethyl-cyclopentylmethyl, ethyl-cyclohexylmethyl, ethyl-cyclopentylethyl,ethyl-cyclohexylethyl, dimethyl-cyclopentylmethyl,dimethyl-cyclohexylmethyl, dimethyl-cyclopentylethyl ordimethyl-cyclohexylethyl, etc..

Hydroxyalkyl preferably encompasses hydroxymethyl, 1-hydroxyethyl,1-hydroxypropyl, 2-hydroxyethyl, 2-hydroxypropyl,2-hydroxy-2-methyl-ethyl, 3-hydroxypropyl and various hydroxybutylradicals.

Alkoxyalkyl is meant to include without limiting the definition thereof:methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl,butyloxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propyloxyethyl,2-isopropyloxyethyl, 2-butyloxyethyl, 1-methoxyethyl, 1-ethoxyethyl,1-propyloxyethyl, 1-isopropyloxyethyl, 1-butyloxyethyl, 1-methoxypropyl,1-ethoxypropyl, 1-propyloxypropyl, 1-isopropyloxypropyl,1-butyloxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propyloxypropyl,2-isopropyloxypropyl, 2-butyloxypropyl, 3-methoxypropyl, 3-ethoxypropyl,3-propyloxypropyl, 3-isopropyloxypropyl, 3-butyloxypropyl, methoxybutyl,ethoxybutyl, propyloxybutyl, and butyloxybutyl.

Alkoxycarbonyl is for example: methoxycarbonyl, ethoxycarbonyl,propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl,s-butyloxycarbonyl, or terbutyloxycarbonyl.

Within this document alkanoyl includes the aliphatic acyl radicals, e.g.formyl, acetyl, propionyl, isopropionyl, butyryl, isobutyryl,sec-butyryl, tert-butyryl, valeryl, isovaleryl, sec-valeryl andpivaloyl. These radicals are frequently employed in the alkanoyloxyalkyland alkanoylaminoalkyl groups as defined for this invention.

Aminoalkyl includes aminomethyl, aminoethyl, aminopropyl, aminobutyl andthe isomeric forms thereof. Likewise alkylaminoalkyl anddialkylaminoalkyl include for example methylaminomethyl,ethylaminomethyl, propylaminomethyl, methylaminoethyl, ethylaminoethyl,propylaminoethyl, methylaminopropyl, ethylaminopropyl,dimethylaminomethyl, dimethylaminoethyl, dimethylaminopropyl.ethyl-methylaminomethyl, ethyl-methylaminoethyl,ethyl-methylaminomethyl, ethyl-methylaminopropyl, etc..

Haloalkyl includes halogenated alkyl, preferably based onC₁-C₆haloalkyl, more preferably on C₁-C₄alkyl, which is linear orbranched, and is substituted by one or more, for example in case ofsubstitution with halogen atoms all hydrogens of the basic hydrocarbonstructure may be replaced by halogen atoms, being all identical ordifferent. Typical examples are CHCl₂, CH₂F, CCl₃, CH₂Cl, CHF₂, CF₃,CH₂CH₂Br, C₂Cl₅, CH₂Br, CHClBr, CF₃CH₂, C₂F₅, C₃F₇, C₄F₉, C₅F₁₁,CH₂CH₂Cl, CH(CH₃)—CH₂—CH₂Cl, CH₂CH₂F, CH(CH₃)—CH₂—CH₂F, C(CH₃)₂—CH₂—Cl,C(CH₃)₂—CH₂—CF₃, C(CH₃)—CH₂—CH₂—CF₃, etc..

Haloalkoxy includes halogenated alkoxy which preferably based onC₁-C₆alkoxy, more preferably on C₁-C₄alkoxy, which is linear orbranched, and is substituted by one or more, for example in the case ofhalo-ethyl up to five halogen atoms. Especially fluorine is preferred asa halogen substituent in alkoxy groups, including trifluoromethoxy and1,1,2,2-tetrafluoroethoxy as prominent members.

Cyanoalkyl includes without limiting the definition thereof:cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl,3-cyanopropyl, 1-cyanoisopropyl, 2-cyanoisopropyl, the isomericcyanobutyl, cyanopentyl and cyanohexyl. Cyanomethyl and cyanoethyl arepreferred.

Aryl typically includes aromatic hydrocarbon rings such as phenyl,naphthyl, anthracenyl, phenanthrenyl and biphenyl, for example1,3-biphenyl and 1,4-biphenyl, with phenyl being preferred. The samedefinition applies where aryl is part of arylalkyl.

The most prominent examples for arylalkyl are benzyl and phenethyl.

Heteroaryl includes aromatic ring systems comprising mono-, bi- ortricyclic systems wherein at least one oxygen, nitrogen or sulfur atomis present as a ring member. The same definition applies whereheteroaryl is part of heteroarylalkyl. Examples are of heteroaryl ringsare furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl,isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl,triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl,triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl,benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl,quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl,cinnolinyl and naphthyridinyl.

The heteroaryl group may be bonded to the basic molecular structure offormula I via a carbon or a nitrogen atom.

Heterocyclyl designates fully or partially hydrogenated heteroaryl ringsystem as outlined above. Typical examples include 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 5-hydroxy-tetrathydrofuran-2-yl, 2-isoxazolinyl,3-isoxazolinyl, 4- isoxazolinyl, 5-isoxazolinyl, pyrrolidin-2-on-5-yl,N-pyrrolidinyl, 2-pyrrolidinyl, 2-pyrrolin-5-yl, etc.

Where the above aryl and heteroaryl groups may be optionallysubstituted, this means that they may carry one or more identical ordifferent substituents. Normally not more than three substituents arepresent at the same time. Examples of substituents of aryl or heteroarylgroups are: amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, halogen,hydroxy, mercapto, cyano, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₂-C₆al-kenyloxy andC₂-C₆alkynyloxy.

Typical examples for substituted aryl include 4-chlorophenyl,4-bromophenyl, 3,4-dichlorophenyl, 4-chloro-3-fluorophenyl,3-chloro-4-fluorophenyl, 4-methylphenyl, 4-ethylphenyl,4-propargyloxyphenyl, 4-allyloxyphenyl, 3,4-dioxomethylenyl-phenyl,3,4-dioxoethylenyl-phenyl, 3-methylphenyl, 4-fluorophenyl,4-ethenylphenyl, 4-ethynylphenyl, 4-propylphenyl, 4-isopropylphenyl,4-tert.butylphenyl, 4-ethoxyphenyl, 4-ethynyloxyphenyl,4-methylmercaptophenyl, 4-methylsulfonylphenyl, 4-cyanophenyl,4-methoxycarbonyl-phenyl, 3-bromophenyl, 3-chlorophenyl, 2-chlorophenyl,2,4-dichlorophenyl, 3,4,5-trichlorophenyl, 3,4-difluorophenyl,3,4-dibromophenyl, 3,4-dimethoxyphenyl, 3,4-dimethylphenyl,3-chloro-4cyanophenyl, 4-chloro-3-cyanophenyl, 3-bromo-4-methylphenyl,4-methoxy-3-methylphenyl, 3-fluoro-4methoxyphenyl,4-chloro-3-methylphenyl, 4-chloro-3-trifluoromethyl-phenyl,4-bromo-3-chlorophenyl, 4-trifluoromethylphenyl,4-trifluoromethoxyphenyl, 4-methoxyphenyl, etc. Typical examples forsubstituted heteroaryl include 5-methyl-2-thienyl, 5-chloro-2-thienyl,3-chloro-2-thienyl, 5-methyl-2-furyl, 4-methyl-oxazol-5-yl,5-hydroxy-pyrazol-1-yl, 5-hydroxy-3-methyl-pyrazol-1-yl,5-amino-3-methyl-pyrazol-1-yl, 5-amino-pyrazol-1-yl,5-methyl-[1,3,4]-oxadiazol-2-yl, 5-ethyl-[1,3,4]-oxadiazol-2-yl,2-amino-thiazol-4-yl, 2-methyl-thiazol4-yl, 6-chloro-pyridin-2-yl,6-amino-pyridin-2-yl, etc..

The N-ring system, being defined for the combination of R₁ and R₂includes primarily simple cyclic secondary amines like pyrrolidinyl,piperidinyl, morpholinyl, thiomorpholinyl and the alkyl-substitutedderivatives, e.g. methyl-morpholinyl and dimethyl-morpholinyl.

The group —N═CR₉—NR₁₀R₁₁ includes the various combinations ofsubstituents for R₉, R₁₀ and R₁₁ including simple structures such as—N═CH—N(CH₃)₂, —N═C(CH₃)—N(CH₃)₂ and —N═C(C₂H₅)—N(CH₃)₂.

The group —CO—R₉ represents an acyl radical which includes a very widevariation of the basic acid. It encompasses formic acid, the alkanoicacids as defined above and the aromatic acids. Typical examples inaddition to the alkanoyl radicals are benzoyl, phenylacetyl,phenylpropionyl, á-methyl-phenylacetyl, nicotinoyl, isonicotinoyl,chlorobenzoyl, trifluoroacetyl, pentafluoropropionyl,heptafluorobutyryl, chloroacetyl, dichloroacetyl, trichloroacetyl,á,á-dimethyl-â-chloropropionyl, cyclopropylcarbonyl, etc.. The samedefinitions apply where —CO—R₉ is part of —O—CO—R₉ or —NH—CO—R₉.

The group —CO—O—R₁₀ represents for example methoxycarbonyl,ethoxycarbonyl, etc.. The group —CO—NR₁₀R₁₁ stands for example formethylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,dimethyl-aminocarbonyl, ethyl-methylaminocarbonyl, diethylaminocarbonyl,etc..

The presence of at least one asymmetric carbon atom in the compounds offormula I means that the compounds may occur in optically isomeric andenantiomeric forms. As a result of the presence of a possible aliphaticC═C double bond, geometric isomerism may also occur. Formula I isintended to include all those possible isomeric forms and mixturesthereof

Certain compounds of formula I are capable of forming acid additionsalts, for example with inorganic acids, such as hydrochloric acid,sulfuric acid or a phosphoric acid, or with suitable organic carboxylicor sulfonic acids, for example aliphatic mono- or di-carboxylic acids,such as trifluoroacetic acid, acetic acid, propionic acid, glycolicacid, succinic acid, maleic acid, fumaric acid, hydroxymaleic acid,maleic acid, tartaric acid, citric acid, oxalic acid or amino acids,such as argentine or lysine, aromatic carboxylic acids, such as benzoicacid, 2-phenoxy-benzoic acid, 2-acetoxy-benzoic acid, salicylic acid,4-aminosalicylic acid, aromatic-aliphatic carboxylic acids, such asmandelic acid or cinnamic acid, heteroaromatic carboxylic acids, such asnicotinic acid or isonicotinic acid, aliphatic sulfonic acids, such asmethane-, ethane- or 2-hydroxy-ethane-sulfonic acid, or aromaticsulfonic acids, for example benzene-, p-toluene- ornaphthalene-2-sulfonic acid.

Formula I according to the invention shall include all the possibleisomeric forms, as well as mixtures, e.g. racemic mixtures, and anymixtures of rotamers.

In view of the close relationship between the compounds of formula I infree form and in the form of their salts, including also salts that canbe used as intermediates, for example in the purification of thecompounds of formula I or in order to identify those compounds,herein-before and hereinafter any reference to the (free) compounds isto be understood as including also the corresponding salts, whereappropriate and expedient.

Among the compounds of formula I according to the present invention thefollowing groups of compounds are preferred. These groups are thosewherein

R₁ is hydrogen, C₁-C₄alkyl or is a group —CO—R₉; or

R₁ is hydrogen, methyl, trifluoroacetyl, pentafluoropropionyl orheptafluorobutyryl; or

R₁ is hydrogen or methyl; or

R₁ is hydrogen, or

R₂ is hydrogen or C₁-C₄alkyl; or

R₂ is hydrogen or methyl; or

R₁ and R₂ are both hydrogen, or

R₁ and R₂ together form the group —N═CR₉—NR₁₀R₁₁; or

R₁ and R₂ together form the groups —N═CH—N(CH₃)₂, —N═C(CH₃)—N(CH₃)₂ or—N═C(C₂H₅)—N(CH₃)₂; or

R₁ and R₂ together form the groups —N═CH—N(CH₃)₂ or —N═C(CH₃)—N(CH₃)₂;or

R₃ is hydrogen ; or

R₄ is hydrogen, hydroxy, amino, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄cyanoalkyl, C₁-C₆alkylamino, di(C₁-C₄alkyl)-amino, C₁-C₆aminoalkyl,halogen, mercapto, cyano, C₁-C₆alkoxy, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,C₁-C₄alkoxycarbonyl, di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, —CO—R₉, or—NH—CO—R₉; or

R₄ is hydrogen, hydroxy, cyano, C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄haloalkyl, C₁-C₄cyanoalkyl, C₁-C₄alkanoyloxy,C₁-C₄hydroxyalkyl, C₁-C₄haloalkanoyloxy, C₁-C₄alkanoyl-C₁-C₆aminoalkyl,C₁-C₄alkanoyloxy-C₁-C₄alkyl, C₁-C₄alkanoyl, C₁-C₄alkylthio orC₁-C₄alkoxycarbonyl; or

R₄ is hydrogen, hydroxy, cyano, fluorine, chlorine, bromine, methyl,tert. butyl, methylthio, trifluoromethyl, cyanomethyl, 2-cyanoethyl,hydroxymethyl, 1-hydroxyethyl, 2-hydroxyisopropyl, acetyl,2-hydroximino-ethyl, 2-methoximino-ethyl, acetoxymethyl,methoxycarbonyl, methoxy, ethoxy or trifluoromethoxy; or

R₅ is hydrogen, hydroxy, methoxy or methylthio; or

R₅ is hydrogen or hydroxy; or

R₅ is hydrogen; or

R₆ is hydrogen, or methoxy; or

R₆is hydrogen; or

R₇ is 4-pyridyl or optionally substituted aryl carrying one to threesubstituents independently selected from the group comprising halogen,C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy; or

R₇ is phenyl or halophenyl; or

R₇ is phenyl, 4-fluorophenyl or 4-chlorophenyl; or

R₈ is hydrogen, C₁-C₄alkanoyl, C₁-C₄haloalkanoyl or C₁-C₄alkyl; or

R₈ is hydrogen or C₁-C₄fluoroalkanoyl; or

R₈ is hydrogen.

Further preferred subgroups of formula I are those compounds wherein:

a) R₃, R₆ and R₈ are all hydrogen, or

b) R₁ is hydrogen, C₁-C₄alkyl, or is a group —CO—R₉; and R₂ is hydrogenor C₁-C₄alkyl; or R₁ and R₂ together form the group —N═CR₉—NR₁₀R₁₁; R₃is hydrogen or methyl; and R₄ is hydrogen, hydroxy, amino, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄cyanoalkyl, C₁-C₆alkylamino, di(C₁-C₄alkyl)-amino,C₁-C₆aminoalkyl, halogen, mercapto, cyano, C₁-C₆alkoxy, C₂-C₆alkenyloxy,C₂-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, C₁-C₄alkoxycarbonyl; —CO—R₉, or—NH—CO—R₉; and R₅ is hydrogen, hydroxy, methoxy or methylthio; and R₆ ishydrogen or methoxy; and R₇ is 4-pyridyl or optionally substituted arylcarrying one to three substituents independently selected from the groupcomprising halogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl andC₁-C₄haloalkoxy; and R₈ is hydrogen, C₁-C₄alkanoyl, C₁-C₄haloalkanoyl orC₁-C₄alkyl; or

c) R₁ is hydrogen, methyl, trifluoroacetyl, pentafluoropropionyl orheptafluorobutyryl; and R₂ is hydrogen or C₁-C₄alkyl; or R₁ and R₂ areboth hydrogen, or R₁ and R₂ together form the groups —N═CH—N(CH₃)₂ or—N═C(CH₃)—N(CH₃)₂; and R₃ is hydrogen or methyl; and R₄ is hydrogen,hydroxy, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄haloalkyl,C₁-C₄cyanoalkyl, C₁-C₄alkanoyloxy, C₁-C₄hydroxyalkyl,C₁-C₄haloalkanoyloxy, C₁-C₄alkanoyl-C₁-C₆aminoalkyl,C₁-C₄alkanoyloxy-C₁-C₄alkyl, C₁-C₄alkanoyl, C₁-C₄alkylthio orC₁-C₄alkoxycarbonyl; and R₅ is hydrogen or hydroxy; and R₆ is hydrogen;and R₇ is phenyl or halophenyl; and R₈ is hydrogen orC₁-C₄fluoroalkanoyl; or

d) R₁ is acetyl; and R₂ is hydrogen or methyl; or R₁ and R₂ togetherform the groups —N═CH—N(CH₃)₂ or —N═C(CH₃)—N(CH₃)₂; and R₃ is hydrogen;and R₄ is hydrogen, hydroxy, cyano, fluorine, chlorine, bromine, methyl,tert. butyl, methylthio, trifluoromethyl, hydroxymethyl, cyanomthyl,2-cyanoethyl, 1-hydroxyethyl, 2-hydroxyisopropyl, acetyl,2-hydroximino-ethyl, 2-methoximino-ethyl, acetoxymethyl,methoxycarbonyl, methoxy, ethoxy or trifluoromethoxy; and R₅ and R₆ arehydrogen; and R₇ is phenyl, 4-fluorophenyl or 4-chlorophenyl; and R₈ ishydrogen or C₁-C₄fluoroalkanoyl; or

e) R₁, R₂, R₃, R₅, R₆ and R₈ are all hydrogen and R₄ is hydrogen,hydroxy, cyano, fluorine, chlorine, bromine, methyl, tert. butyl,methylthio, trifluoromethyl, cyanomethyl, 2-cyanoethyl, hydroxymethyl,1-hydroxyethyl, 2-hydroxyisopropyl, acetyl, 2-hydroximino-ethyl,2-methoximino-ethyl, acetoxymethyl, and R₇ is phenyl, 4-fluorophenyl or4-chlorophenyl.

Other preferred subgroups are characterized by subformula IA

wherein R₁ is hydrogen, C₁-C₄alkyl, or is a group —CO—R₉ or —CO—OR₁₀;and R₂ is hydrogen or C₁-C₄alkyl; or R₁ and R₂ together form the group—N═CR₉—NR₁₀R₁₁; and R₄ is hydrogen, cyano, hydroxy, C₁-C₄alkoxy,C₁-C₆aminoalkyl, C₁-C₈alkanoyloxy-C₁-C₄alkyl,C₁-C₈alkanoylamino-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆hydroxyalkylor C₁-C₄cyanoalkyl, and R₉ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl,C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl, aryl, aryl-C₁-C₄alkyl, heteroarylor heteroaryl-C₁-C₄alkyl; R₁₀ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl or C₁-C₄alkoxy-C₁-C₆alkyl; and R₁₂ ishalogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy,and R₁₃ is C₁-C₄alkyl; or by subformula IB

wherein R₄ is hydrogen, hydroxy, cyano, C₁-C₄alkoxy, C₁-C₆aminoalkyl,C₁-C₈alkanoyloxy-C₁-C₄alkyl, C₁-C₈alkanoylamino-C₁-C₄alkyl,C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆hydroxyalkyl or C₁-C₄cyanoalkyl, and R₁₂ ishalogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy.

Preferred individual compounds of the formula I

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine,N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxyethyl)-phenyl]-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxyethyl)-phenyl]-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;N-[4-(2-amino-4-phenyl,thiazol-5-yl)-pyrimidin-2-yl]-N-(3-acetyl-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetyl-phenyl)-amine;N-[4-(2-amino-4-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-(3-cyano-phenyl)-amine;{4-[2-acetylamino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetoxymethyl-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-methoxy-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(4-fluoro-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyano-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyanomethyl-phenyl)-amine;andN-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyanomethyl-phenyl)-amine.

The compounds according to the invention may be prepared according tomethods per se known in the art (this means that in spite of employinggenerally known types of organic reaction steps , that where novelcompounds are produced, the respective process of manufacture and thesequence of steps is novel because it has not been known for beemployable for the novel compound). The procedures for the preparationof compounds of formula I may be outlined as follows:

As shown in Scheme 1 the compounds of formula I may be obtained byreaction of compounds of formula II wherein R₁ and R₂ are as defined forformula I, Y stands for a leaving group such as halogen, alkylthio,alkylsulfinyl, alkylsulfonyl and Z is a leaving group such as halogen,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl, with ananiline of the displayed formula wherein R₃, R₄, R₅, R₆ and R₈ are asdefined for formula I. In this reaction the leaving group Y issubstituted with the aniline of the shown formula.

The anilines with substituents R₃, R₄, R₅, R₆ and R₈ are mostlycommercially available or otherwise can easily be obtained fromcommercial products by per se known processes. The thiazolyl pyrimidinesof formula II have especially been developed for the synthesis of thecompounds of formula I and thus comprise another feature of the presentinvention.

The nucleophilic substitution of a group Y is typically conducted in thepresence of a Lewis acid using an excess of aniline. Y stands for aleaving group, such as halogen, alkylthio, alkylsulfinyl oralkylsulfonyl. The reaction may be carried out in an inert solvent, suchas ethers like tetrahydrofuran, dioxane, diglyme and the like.Appropriate reaction conditions are described for analogous reactionse.g. in U.S. Pat. Nos. 5,670,527 or 5,658,903.

Typical Lewis acids include boron trifluoride, zinc halogenides andsulfonic acids like benzenesulfonic, toluenesulfonic, methanesulfonicand ethanesulfonic acids. The reaction temperature may vary within wideranges, e.g. from +20° C. to +220° C., but mostly is performed at theboiling point of the reaction mixture.

The leaving groups are the standard ones commonly used in organicsynthesis. The relative reactivity of the leaving group X can forexamples be modulated by oxidation of the alkylthio group to thecorresponding more reactive sulfoxide or sulfone using standardconditions.

The compounds of formula II are novel and may be prepared by reacting acompound of the formula III with a thiourea IV. This reaction is in theliterature referred to as Hantzsch thiazole synthesis and may beperformed under reaction conditions described in the literature for thistype of ring formation. The thioureas of formula IV are commercialproducts, or may be synthesized according to known processes.

The intermediate α-halogen-β-pyrimidinylacetyl derivatives of formula mare likewise novel and have been developed for the synthesis of thefinal active ingredients of this invention. The intermediates of formulaIII may be prepared by reacting an analogous β-pyrimidinylacetylderivative of formula V with a halogenating agent. R₇ is as defined forformula I and Hal stands for a halogen atom, preferably bromine orchlorine. Typical halogenating agents include bromine and chlorine andits addition compounds with amines as well as copper bromide and thelike. The reaction is preferably conducted in an organic solvent, suchas acetic acid, alcohols or halogenated hydrocarbons, such as chloroformor methylene chloride. The reaction temperature may vary from −20° C. toboiling temperature of the reaction mixture, depending on the reactivityof the halogenated compound of formula V. It is typically close to roomtemperature.

Compounds of the general formula V wherein R₇ is as defined for formulaI may be prepared by reacting a methylpyrimidine of the formula VI witha carbonic acid derivative of formula VII. The radical X in formula VIIstands for a leaving group such as alkoxide, dialkylamine, dialkylhydroxylamine, halogen and acyloxy. Many of the α-pyrimidinylacetylderivatives of formula V are known, and the still novel ones can beobtained according to known methods. The starting materials VI and VIIare known compounds.

The first reaction step of Scheme 1 is a type of Claisen type estercondensation. The condensation is achieved in the presence of strongbases, including alkoxides, such as potassium t-butoxide or sodiumt-butoxide, lithiumamides, such as LDA or LiHMDS and metal hydrides,such as potassium or sodium hydride, and is preferably conducted in aninert solvent. Typical solvents are ethers, such as diethylether, glymeand THF. In certain cases the use of more polar solvents, such as DMF,DMSO and HMPT is preferred. The reaction is typically performed attemperatures ranging from −78° C. to the boiling point of the solvent.

For reasons of laboratory convenience and rationalization of work, areasonable approach is to start the synthesis of compounds of formula Iwith thiourea (intermediate IV wherein R₁ and R₂ are hydrogen) and tomodify the amino group NR₁R₂ on the stage of the intermediate of formulaII by conducting a Sandmeyer replacement reaction according to Subscheme1a followed by displacement of halogen by an amine HNR₁R₂.

In Subscheme 1a the radicals are defined as in Scheme 1.

Alternatively, the compounds of formula I may be obtained according toSchemes 2 and 3.

According to Scheme 2 the compounds of formula I may be obtained byreaction of compounds of formula VIII wherein R₃, R₄, R₅, R₆, R₇ and R₈are as defined for formula I and Z is a leaving group such as halogen,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl with an amineHNR₁R₂. The intermediates of formula VIII represent another feature ofthe present invention.

This amination reaction with a secondary amine HNR₁R₂ is a typicalnucleophilic substitution reaction and may be carried out under theconditions known as common for such reactions. The reaction may becarried out in an inert solvent, such as ethers, dimethylformamide,dimethylsulfoxide, alcohols, acetonitrile, and the like.

For the case that nucleophilic amines are used, this reaction will workwithout the presence of an additional base; however, when more acidicamines are employed a base may be required. Typical bases includealkaline carbonates, such as potassium carbonate and sodium carbonate ormetal alcoholates, such as potassium tert-butoxide. The reactiontemperature may vary within wide ranges, e.g. from room temperature to+150° C. In the case of Z being alkylthio the reactivity of theintermediate starting material VII may be enhanced by oxidizing theleaving group W to the corresponding sulfoxide or sulfone using standardconditions for such transformations.

The intermediates of formula VIII may in turn be obtained by reacting acompound of formula IX wherein R₇ is defined as for formula I, W standsfor a secondary amino group, wherein the two radicals are eitherC₁-C₄alkyl or together form an alkylene chain, with dimethylamino beingthe preferred embodiment, and Z is as defined for formula VIII, and witha guanidine of formula X wherein the substituents R₃, R₄, R₅, R₆ and R₈are as defined for formula I.

The guanidines of formula X are known in the art, and are evencommercially available. In contrast, the intermediates of formula IX arenovel and yet stand for another feature of the present invention, and sois the preceding intermediate of formula XI which had to be especiallycreated in order to enable this synthesis pathway of the activeingredients of formula I.

This cyclization reaction step (IX+X?VIII) may be carried out in thepresence or absence of a solvent. The presence of a solvent is preferredin laboratory scale, while technical scale production prefers thevariants without use of solvents. Typical solvents for this step wouldinclude alcohols, such as ethanol, iso-propanol, iso-butanol and thelike, dimethylformamide, ethers, such as dioxane and hydrocarbons, suchas toluene. In case where the guanidine VIII is used in form of anaddition salt other then a hydrogen carbonate the addition of anadditional base as co-reagent is required. The reaction temperature mayvary within narrow ranges, but is principally defined by the boilingtemperature of the reaction mixture. Typically, such temperatures arebetween +80° C. and +150° C.

The compounds of the general formula IX as defined above may be obtainedby reacting an acetyl thiazole compound of formula XI with adialkyl-formamide acetal, such as dimethylformamide dimethyl acetal ordimethylacetamide acetal. Alkyl in Scheme 2 represents C₁-C₄alkyl, e.g.methyl while alkylene is a straight or branched C₁-C₅hydrocarbon bridgelike methylene, ethylene, methylethylene, ethylethylene ordimethylethylene. Where desired a solvent may be used. Typical solventsinclude dimethylformamide and dioxane. The reaction temperature liestypically between +80° C. and +120° C.

Compounds of the general formula XI may be obtained by metallating athiazole of the formula XII with a metallating agent such asalkyllithium and reacting it with an acetylating agent AcT wherein T isa leaving group being typically the N,O-dimethylhydroxylamino radical(Weinrebs amide), or otherwise preferably N,N-dimethylamino. Metallationis performed in a inert solvent, such as ethers like diethyl ether,tetrahydrofuran or alkanes and mixtures thereof. The metallating agentis typically butyllithium. The reaction temperature lies in the range of−78° C. to 0C. The metallated transitional intermediate formed from thethiazole is in this reaction quenched with an acyl equivalent AcT. Thethiazole compounds of formula XII is described in literature.

Alternatively compounds of formula XI, where Z stands for C₁-C₄alkylthioor optionally substituted amino can be prepared by reacting a compoundof formula XIV with halogenated acetone, e.g. bromoacetone. Thecompounds of formula XIV are known in the art.

The Negishi type coupling reaction allows to build up the basicstructure of the active ingredients of formula I in a different manner.This may have advantages for some specific substitution patterns informula I.

In Scheme 3 the radicals are as defined above. The reaction conditionsmay in general correspond to the following:

Deprotection of compounds of the general formula VIII to form compoundsof the formula I may be accomplished by treating a compound of thegeneral formula VIII with an acid using standard conditions.

Compounds of the general formula VIII may be obtained in accordance toScheme 1 by displacement of iodine by an aniline under reactionconditions already described above.

Compounds of the general formula XVI may be obtained by reacting anaminothiazole XV according to the method of Negishi. Thus a compound offormula XV is allowed to react with a metallating agent, such asn-hexyllithium or n-butyllithium, in an inert solvent, such as etherslike tetrahydrofuran, glyme, diethyl ether and the like, to give adilithiated intermediate. The reaction temperature may vary withinranges. It typically lies between −78° C. to 0C. The lithiated speciesis in-situ transmetallated using at least stoichiometric amounts of azinc salt, such as zinc chloride or zinc bromide. The thus obtained zinccompound may then be reacted with 2,4-diiodopyrimidine in the presenceof a palladium catalyst. Typical palladium catalysts include Pd(PPh₃)₄or Pd₂dba₃. The reaction temperature of the coupling lies in the rangeof 0° C. to the boiling point of the reaction mixture.

For various reasons it may also be desirable to transform one derivativeof formula I into another one which is also within the generaldefinition of formula I.

Thus, it is for example possible to acylate compounds of the subformulaIa wherein R₁ is hydrogen using acylating agents.

Typical acylation agents for this purpose include carboxylic acidchlorides, carboxylic acid anhydrides, chloroalkyl formiates,carbamoylchlorides and the like. The acylation may be carried out in thepresence or absence of a base. The reaction temperature will suitablylie in the range from 0° C. to the boiling point of the reactionmixture. Inert solvents may be used where desired or indicated by thenature of the reagents. Examples of suitable bases include alkalinemetal carbonates or bicarbonates, such as potassium carbonate or sodiumhydrogen carbonate (referred to as Schotten-Baumann conditions) ortertiary amines, such as triethylamine or diisopropylethylamine.Examples of suitable solvents include aromatic hydrocarbons such astoluene; ethers such as diethyl ether, tetrahydrofuran and glyme ormixtures with water.

If in the compound of formula Ia R₂ is hydrogen, and depending on thenucleophilicity of the acylating agent and the reaction conditions notonly mono- but also diacylated products can be obtained. Therein R₁ andR₂ independently of each other stand for identical or different —CO—R₉moieties. Where the diacylated product appears as a by-product to themonoacylated compound of formula Ia, the product mixtures can beseparated by crystallization or chromatography.

Derivatives of the subformula Ib

may be modified if desireda) by reacting them with an amide acetal. Typical amide acetals includedimethylformamide acetal and dimethylacetamide acetal. The reaction istypically carried out with the pure reagents, i.e. without the presenceof a solvent. Where desired, also inert solvents such asdimethylformamide or ethers, such as tetrahydrofuran, glyme or dioxane,or esters may be used. The reaction temperature lies in the range fromabout +50° C. to the boiling point of the mixture. orb) by alkylating them in a reaction where the compound of formula Ib istreated with an aldehyde in the presence of a reducing agent (in theliterature referred to as reductive alkylation). This reaction is withadvantage performed in a solvent. Typical solvents include ethers, suchas tetrahydrofuran, glyme, acetic acid or alcohols. Reducing agentsinclude borohydrides, such as sodium borohydride and sodiumcyanoborohydride. The reaction temperature lies in the range from 0° C.to the boiling point of the solvent.

Further derivatives of the formula I may be easily obtained fromreacting the compounds of subformula Ic

at the functional carbonylic group in R₄, e.g. with Grignard-reagentsand other metallated radicals to yield the corresponding tertiaryalcohols. The reaction of this type is routinely performed in inertsolvents and with using an excess of metallated agent. Typical solventsare ethers such as diethyl ether, tetrahydrofuran, glyme and the like.The reaction temperature lies in the range of 0° C. to the boiling pointof the solvent, but is normally kept under strict control by cooling andslow addition of the reactant of formula Ic. The standard work-upprocesses allow to isolate the compounds of formula I, wherein R₄ ishydroxyalkyl in high yields and as pure compounds.

When employing the functional intermediate of formula Id

additional transition metal catalyzed reactions, such as Sonogashira,Heck, Stille and Suzuki couplings, as well as Hartwig-Buchwaldaminations offer further opportunities for derivatization of alreadyprepared compounds of formula I. The indicated methods are known in theart and may be suitably adapted to the requirements of the envisagedderivatization.

In addition to the novel active fungicidal compounds the presentinvention also relates to novel starting materials and/or intermediatesand to processes for the preparation thereof. The starting materialsused and the reaction conditions chosen are preferably such that thecompounds shown in this disclosure as being especially preferred or tobe used preferably are obtained. Especially preferred among the processconditions are those described in the examples below, or analogousprocedures.

The invention also relates to compositions which comprise the compoundsof the formula I, or a salt thereof, as an active component, inparticular plant-protecting compositions, and also to their use in theagricultural sector or related areas.

Active compounds of the formula I are customarily used in the form ofcompositions and may be added, simultaneously or successively, to thesurface or plant to be treated together with additional activecompounds. These additional active compounds may be either fertilizers,trace element-supplying agents or other preparations which influenceplant growth. It is also possible, in this context, to use selectiveherbicides, such as insecticides, fungicides, bactericides, nematicidesor molluscicides, or mixtures of several of these preparations,additionally, where appropriate, together with excipients, surfactantsor other administration-promoting additives which are customary informulation technology (designated collectively as carrier materialsherein).

Suitable excipients and additives may be solid or liquid and are thosesubstances which are appropriate in formulation technology, for examplenatural or regenerated minerals, solvents, dispersants, wetting agents,adhesives, thickening agents, binding agents or fertilizers.

A preferred method for applying a compound of formula I, or anagrochemical composition which comprises at least one of thesecompounds, is administration to the leaves (foliar application). Thefrequency and rate of administration depend upon the risk of infestationby the corresponding pathogen. The compounds of formula I can, however,also penetrate the plant through the roots via the soil (systemicaction). If the locus of the plant is impregnated with a liquidformulation or if the substances are introduced in solid form into thesoil, e.g. in the form of granules (soil application). In paddy ricecrops, such granules can be applied in metered amounts to the floodedrice fields. In order to treat seeds , the compounds of formula I can,however, also be applied to the seeds (coating), either by impregnatingthe grains or tubers with a liquid formulation of the active ingredient,or by coating them with a solid formulation.

Advantageous rates of application are in normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kgof a.i./ha, especially from 20 g to 600 g a.i./ha. When the compound areused as seed dressings, dosages of from 10 mg to 1 g of activeingredient per kg seed are advantageous employed. The agrochemicalcompositions generally comprise 0.1 to 99% by weight, preferably 0.1 to95% by weight, of a compound of formula I, 99.9 to 1% by weight,preferably 99.8 to 5% by weight, of a solid or liquid adjuvant and 0 to25% by weight, preferably 0.1 to 25% by weight, of a surfactant. Whereascommercial products will preferably be formulated as concentrates, theend user will normally employ dilute formulations.

The compositions may also comprise further auxiliaries, such asfertilizers and other active ingredients for obtaining special desirablebiological effects.

The compounds of formula I may be used preventatively and/or curativelyin the sector of agronomics and related technical areas as activeingredients for controlling plant pests. The active ingredients offormula I according to the invention are notable for their good activityeven at low concentrations, for their good plant tolerance and for theirenvironmentally friendly nature. They have very advantageous, especiallysystemic, properties and may be used to protect a plurality ofcultivated plants. Using the active ingredients of formula I on plantsor plant parts (fruit, flowers, leaves, stems, tubers, roots) of variouscrops, the pests appearing can be controlled or destroyed, whereby theparts of plants which grow later also remain protected, e.g. fromphytopathogenic microorganisms.

The compounds I may additionally be used as a dressing to treat seeds(fruits, tubers, corns) and plant cuttings to protect against fungalinfections and against phytopathogenic fungi occurring in the soil.

The compounds I are effective for example against the following classesof related phytopathogenic fungi: Fungi imperfecti (e.g. Botrytis,Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora andAlternaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia);Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia,Uncinula) and Oomycetes (e.g. Phylophthora, Pythium, Plasmopara).

Target crops for the plant-protecting usage in terms of the inventionare for example the following plant cultivars: cereals (wheat, barley,rye, oats, rice, maize, sorghum and related species); beet (sugar beetand fodder beet); pome, stone and berry fruit (apples, pears, plums,peaches, almonds, cherries, strawberries, raspberries and blackberries);legumes (beans, lentils, peas, soya); oil crops (rape, mustard, poppy,olives, sunflowers, coconut, castor oil, cocoa, peanut); cucumber plants(squashes, cucumber, melons); citrus fruits (oranges, lemons,grapefruits, mandarines); vegetables (spinach, lettuce, asparagus,cabbage varieties, carrots, onions, tomatoes, potatoes, paprika);laurels (avocado, cinnamonium, camphor) and plants such as tobacco,nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananasand natural rubber plants, as well as ornamental plants.

Further areas of application for the active ingredients according to theinvention are the protection of stores and material, where the storagematter is protected against putrescence and mould.

The compounds I are used in unchanged form or preferably together withcustomary excipients in formulation techniques. To this end, they areconveniently processed in known manner e.g. into emulsion concentrates,coatable pastes, directly sprayable or diluable solutions, dilutedemulsions, wettable powders, soluble powders, dusts or granules, e.g. byencapsulation into for example polymeric materials. As with the type ofmedium, the application processes, such as spraying, atomizing, dusting,scattering, coating or pouring are similarly chosen according to thedesired aims and the prevailing conditions.

Suitable substrates and additives may be solid or liquid and are usefulsubstances in formulation techniques, e.g. natural or regeneratedmineral substances, dissolving aids, dispersants, wetting agents,tackifiers, thickeners or binding agents.

The compounds of formula I may be mixed with further active ingredients,e.g. fertilizers, ingredients providing trace elements or other activeingredients used in the plant protection science, especially furtherfungicides. In doing so, in some cases synergistic enhancement of thebiological effects may occur.

Preferred active ingredients advantageous as additives to thecompositions comprising the active ingredient of formula I are:

Azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole,cyproconazole, difenoconazole, diniconazole, epoxiconazole,fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole,imazalil, imibenconazole, ipconazole, metconazole, myclobutanil,pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole,simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,triflumizole, triticonazole; pyrimidinyl carbinoles, such as ancymidol,fenarimol, nuarimol; 2-amino-pyrimidines, such as bupirimate,dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine,fenpropimorph, spiroxamine, tridemorph; anilinopyrimidines, such ascyprodinil, mepanipyrim, pyrimethanil; pyrroles, such as fenpiclonil,fludioxonil; phenylamides, such as benalaxyl, furalaxyl, metalaxyl,R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl,carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, suchas chlozolinate, dichlozoline, iprodione, myclozoline, procymidone,vinclozoline; carboxamides, such as carboxin, fenfuram, flutolanil,mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine,dodine, iminoctadine; strobilurines, such as azoxystrobin,kresoxim-methyl, metominostrobin, SSF-129, trifloxystrobin,picoxystrobin, BAS 500F (proposed name pyraclostrobin), BAS 520;dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb,thiram, zineb, ziram; N-halomethylthiotetrahydrophthalimides, such ascaptafol, captan, dichlofluanid, fluorornides, folpet, tolyfluanid;Cu-compounds, such as Bordeaux mixture, copper hydroxide, copperoxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper;nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl;organo-p-derivatives, such as edifenphos, iprobenphos, isoprothiolane,phosdiphen, pyrazophos, tolclofos-methyl; various others, such asacibenzolar-S-methyl, anilazine, benthiavalicarb, blasticidin-S,chinomethionate, chloroneb, chlorothalonil, cyflufenamid, cymoxanil,dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, SYP-LI90(proposed name: flumorph), dithianon, ethaboxam, etridiazole,famoxadone, fenamidone, fenoxanil, fentin, ferimzone, fluazinam,flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb,IKF-916 (cyazofamid), kasugamycin, methasulfocarb, metrafenone,nicobifen, pencycuron, phthalide, polyoxins, probenazole, propamocarb,pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole,triforine, validamycin, zoxamide (RH7281).

One preferred method of application of an active ingredient of formula Ior of an agrochemical composition containing at least one of theseactive ingredients is foliar application. The frequency and amount ofapplication depend on the severity of the attack by the pathogen inquestion. However, the active ingredients I may also reach the plantsthrough the root system via the soil (systemic action) by drenching thelocus of the plant with a liquid preparation or by incorporating thesubstances into the soil in solid form, e.g. in the form of granules(soil application). In rice cultivations, these granules may bedispensed over the flooded paddy field. The compounds I may however alsobe applied to seed grain to treat seed material (coating), whereby thegrains or tubers are either drenched in a liquid preparation of theactive ingredient or coated with a solid preparation.

The compositions are produced in known manner, e.g. by intimately mixingand/or grinding the active ingredient with extenders such as solvents,solid carriers and optionally surfactants.

Favorable application rates are in general 1 g to 2 kg of activesubstance (AS) per hectare (ha), preferably 10 g to 1 kg AS/ha,especially 20 g to 600 g AS/ha. For usage as a seed dressing, it isadvantageous to use dosages of 10 mg to 1 g active substance per kg ofseed grain.

While concentrated compositions are preferred for commercial usage, theend user normally uses diluted compositions.

Formulations may be prepared analogously to those described for examplein WO 97/33890.

EXAMPLES

The subsequent examples are intended to illustrate the invention,without however limiting the scope thereof.

Synthesis Example 1N-{4-[2-(1-Dimethylamino-ethylimino)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine

a) 2-(2-Methylthio-pyrimidin-4-yl) 1-phenyl-ethanone

A mixture of 4-methyl-2-methylthio-pyrimidine (30 g, 0.21 mol) andmethyl benzoate (30 g, 0.21 mol) is added to a solution of potassiumtert-butoxide (54 g, 0.48 mol) in tetrahydrofuran (350 ml) with coolingin such a way that the reaction temperature does not exceed +20° C.After stirring the mixture for additional 20 minutes the solution ispoured onto crushed ice. The resulting solution is acidified withconcentrated hydrochloric acid and extracted with ethyl acetate. Dryingof the organic phase, filtering and evaporation of the solvent underreduced pressure gives the2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone in form of a mixtureof tautomers.b) 2-Bromo-2-(2-methylthio-primidin-4-yl)-1-phenyl-ethanone

Bromine (24.1 g, 0.15 mol) is added with stirring to2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone (36.8 g, 0.15 mol) inacetic acid (300 ml) in such a way that the reaction temperature doesnot exceed +25° C. and the color of the bromine is dischargedimmediately. After the addition of the bromine solution the solvent isremoved by evaporation under vacuum. The pH of the resulting oil isadjusted to 8 using an aqueous saturated sodium bicarbonate solution andthe product is extracted several times with diethylther. Drying thecombined extracts with magnesium sulfate, filtering and evaporation ofthe solvent gives the crude2-bromo-2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone in form of anoil of sufficient purity for the following step.c) 4-(2-Amino4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine

A solution of 2-bromo-2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone(45 g, 0.14 mol) and thiourea (21.2 g, 0.28 mol) in ethanol (300 ml) isheated at reflux for 4 hours. On cooling the product starts tocrystallize as salt. It is filtered with suction and washed with ether.The free amine is obtained by partitioning of the product between anaqueous solution of sodium bicarbonate and a 1:1 mixture of ethylacetate and tetrahydrofuran, followed by drying of the organic phaseover magnesium sulfate, filtering and evaporation of the solvents. The4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine is obtained incrystalline form, m.p. 208-209° C.d) 4-(2-Amino-4-phenyl-thiazol-5-yl)-2-methylsulfinvl-pyrimidine

A suspension of4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylthio-pyrimidine (16.5 g, 0.055mol) in methylene chloride (350 ml) is cooled to 0° C. After theaddition of m-chloro perbenzoic acid (14.9 g, content of 70% peracid,0.06 mol) in 5 portions the resulting solution is stirred for anadditional hour. The reaction mixture is neutralized by addition of asaturated aqueous solution of sodium bicarbonate yielding a crystallinesuspension of the product. After addition of hexane the precipitated4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine isfiltered with suction, washed with water and diethyl ether and finallydried at +50° C. under high vacuum.e) N-[4-(2-Amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine

A mixture of4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine (0.5 g,1.58 mmol) and aniline (1.5 g, 15.8 mmol) is heated at +100° C. Afterthe addition of boron trifluoride diethyl etherate (3 drops) thesolution is heated at +150° C. for half an hour. On cooling the productstarts to crystallize. The crystals are filtered and washed thoroughlywith diethyl ether to give theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine inpure form, having a m.p. of 244-245° C.f) A suspension of[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-phenyl-amnine (0.28g, 0.81 mmol) in dimethylacetamide dimethylacetal (0.22 g, 1.62 mmol)and dimethylformamide (10 ml) is heated at 140° C. for 4 hours. Afterdistilling off all volatile compounds the residue is purified bychromatography on silicagel (eluent: ethyl acetate/hexane) to give inform of a yellow powder, m.p. 196-197° C.

Synthesis Example 2N-[4-(2-Acetylamino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-Nphenyl-amnine

A suspension ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine(0.25 g, 0.7 mmol), acetic acid anhydride (0.11 mg, 1.1 mmol),triethylamine (0.11 mg, 1.1 mmol) and a catalytic amount ofN,N-dimethylaminopyridine is heated at reflux for 18 hours. Thevolatiles are evaporated under reduced pressure and the product iscrystallized by the addition of diethyl ether. Filtering and dryinggives theN-[4-(2-acetylamino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine,m.p. >260° C.

Synthesis Example 3N-{4-[2-(3-Methylbutyl-amino)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine

Sodium cyanoborohydride (92 mg, 1.3 mmol) is added at room temperatureto a suspension ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine (150mg, 0.4 mmol) and isovalerianaldehyde (113 mg, 1.3 mmol) in a mixture ofmethanol (13 ml), acetic acid (0.3 ml) and water (0.05 ml). The reactionmixture is stirred at room temperature for 18 hours. Partitioning of themixture between water and ethyl acetate, drying over magnesium sulfate,filtering and evaporating of the solvents under reduced pressure givesthe crude product. After crystallization from a mixture of diethyl etherand hexane theN-{4-[2-(3-methylbutyl-amino)4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-aminehas a m.p. of 170-172° C.

Synthesis Example 4N-[4-(2-Amino4-phenyl-thiazol-5-yl)-primidin-2-yl]-N-[3-(3-hydroxy-3-methyl-1-butynyl)-phenyl]-amine

a)N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine

A mixture of5-(2-methylsulfinyl-pyrimidin-4-yl)-4-phenyl-2-amino-thiazole (2.0 g,6.3 mmol) and m-iodoaniline (7.0 g, 31.6 mmol) is heated at +100° C.After the addition of boron trifluoride diethyl etherate (3 drops) thesolution is heated at +150° C. for half an hour. On cooling the productstarts to crystallize. TheN-[4(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amineafter chromatography (eluent: 2:1 mixture of ethyl acetate/hexane) has am.p. of 243-244° C.b) A suspension ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine(300 mg, 0.64 mmol) and 2-methyl-3-butyn-2-ol (110 mg, 1.3 mmol) indimethylformamide (20 ml) and diisopropylamine (5 ml) are stirred in thepresence of bis triphenylphosphine palladiumdichloride (20 mg),triphenylphosphine (20 mg) and copper iodide under a nitrogen atmospherefor 16 hours. After an aqueous work-up the residue is purified bychromatography (eluent: 1:2 mixture of ethyl acetate/hexane) to give theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(3-hydroxy-3-methyl-1-butynyl)-phenyl]-amine,m.p. 262-263° C.

Synthesis Example 5N-[4-(2-Amino-4:phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3′,4′-dimethoxy-biphenyl-3-yl)-amine

A solution ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine(300 mg, 0.64 mmol) and 3,4-dimethoxyphenylboronic acid (122 mg, 0.66mmol) in dimethoxyethane (8 ml) and aqueous potassium carbonate (13 ml)are stirred in the presence of tetrakis triphenylphosphine palladium (15mg) under a nitrogen atmosphere at reflux for 1 hour. After an aqueouswork-up the residue is purified by chromatography (eluent: 2:1 mixtureof ethyl acetate/hexane) to give theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3′,4′-dimethoxy-biphenyl-3-yl)-amine,m.p. 236-237° C.

Synthesis Example 6N-[4-(2-Amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(2-hydroxy-2-methyl-ethyl)-phenyl]-amine

a)N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxycarbonyl-phenyl)-amineA mixture of2-amino-4-phenyl-5-(2-methylsulfinyl-pyrimidin-4-yl)-thiazole (2.0 g,6.3 mmol) and m-amino benzoic acid methyl ester (13.0 g, 90mmol) isheated at +100° C. After the addition of boron trifluoride diethyletherate (3 drops) the solution is heated at +150° C. for half an hour.After chromatography (eluent: ethyl acetate/hexane) theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxycarbonyl-phenyl)-aminehas a m.p. of 223-225° C.b) To a suspension ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxycarbonyl-phenyl)-amine(800 mg, 2.0 mmol) in tetrahydrofuran (30 ml) is added a solution ofmethyl magnesium chloride (6 ml of a 20% THF solution) without cooling.The temperature of the reaction mixture rises to about +45° C. and thestarting material dissolves immediately yielding a yellow clearsolution. After an additional hour the solution is poured onto crushedice and ammonium chloride. The colorless precipitate is filtered andwashed with ethyl acetate and tetrahydrofuran. The organic phases arepooled, dried and concentrated under reduced pressure. Chromatography ofthe resulting solid gives theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(2-hydroxy-2-methyl-ethyl)-phenyl]-amine,m.p. 219-220° C.

Synthesis Example 7N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-hydroxymethyl-phenyl)-amine

To a suspension ofN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxycarbonyl-phenyl)-amine(800 mg, 2.0 mmol) in tetrahydrofuran (25 ml) is added a solution ofsodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (3 ml of a 3.5Msolution) without cooling. The temperature of the reaction mixture risesto about +40° C. and the starting material dissolves immediatelyyielding a yellow clear solution. After an additional hour the solutionis poured onto crushed ice and ammonium chloride. The colorlessprecipitate is filtered and washed with ethyl acetate andtetrahydrofuran. The organic phases are pooled, dried and concentratedunder reduced pressure. Chromatography of the resulting solid gives theN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-hydroxymethyl-phenyl)-amine,m.p. 214-215° C.

Synthesis Example 8N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-Yl]-N-phenyl-amine

a) 2-[N,N-bis(2,2-Dimethylethoxycarbonyl)]-amino]-4-phenyl-thiazole

2-Amino-4-phenyl-thiazole (5.0 g, 28.4 mmol) is solved in 200 ml of dryTHF and a solution of di-tert-butyl pyrocarbonate (13.6 g, 62.5 mmol) inTHF is slowly (dropwise) added. A catalytic amount of DMAP is added tothe reaction mixture before heating it to reflux for 12 hours. Work-up:after cooling to +25° C. the reaction solution is poured on ice,acidified with 2N HCl and extracted with diethylether. The organic phaseis separated, dried with Na₂SO₄, filtered and the solvent is evaporated.The residue is purified by chromatography over silica gel (eluent:PE/EE=20:1). The2-[N,N-bis(2,2-dimethylethoxycarbonyl)-amino]-4-phenyl-thiazole isobtained in form of a highly viscous oil.

¹H-NMR (CDCl₃): 1.48 (s, 18H, CH₃), 7.18 (s, 1H, H-5), 7.22-7.35 (m, 3H,H-3′,4′), 7.79 (d, 2H, H-2′)b) 2-(2,2-Dimethylethoxycarbonyl-amino)4-phenyl-thiazole

The 2-[N,N-bis(2,2-dimethylethoxycarbonyl)-amino]-4phenyl-thiazole (10.7g, 28.4 mmol) is suspended in 100 mL of dry CH₂Cl₂ and 5 equivalents oftrifluoroacetic acid are added. The mixture is stirred at +25° C. whiletest samples are taken and analyzed by TLC until no starting material isleft.Work-up: The reaction mixture is poured into water, basified withsaturated aqueous Na₂CO₃-solution and extracted with CH₂Cl₂. The organicphases are combined, washed with saturated aqueous NaHCO₃-solution andsaturated brine, dried with Na₂SO₄. The solvent is evaporated and theresidue is dried in high vacuum. This quantitative obtained crudeintermediate2-[N,N-bis(2,2-dimethylethoxycarbonyl)-amino-4-phenylthiazole isdirectly used for the following reaction step.

Yield: yellow highly viscous residue that builds a foam and solidifieswhen the last traces of solvent are evaporated, having a m.p.: 65-70° C.¹H-NMR (CDCl₃): 1.20 (s, 9H, C(CH₃)₃), 7.04 (s, 1H, H-5), 7.20-7.38 (m,3H, H-3′,4′), 7.70-7.80 (d, 2H, H-2′, J_(2′3′)=20 Hz)c)4-[2-(2,2-Dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidine

The 2-[N,N-bis(2,2-dimethylethoxycarbonyl)-amino-4-phenyl-thiazole (0.50g, 1.89 mmol) is solved under a nitrogen atmosphere in 35 mL of dry THF.The solution is cooled to −78° C. and a solution of n-BuLi in hexane(4.16 mmol) is added. The mixture is allowed to warm to −20° C. andstirred for 1.5 hours at this temperature. Then the mixture is againcooled to −78° C. and pre-dried ZnCl₂ (0.28 g, 2.08 mmol) in a smallvolume of dry THF is added dropwise at a rate which allows to keep thetemperature of the mixture below −60° C. During the following 1.5 hoursthe mixture is warmed to +25° C., Pd(PPh₃)₄ (0.011 g) and2,4-diiodopyrimidine (0.63 g, 1.89 mmol) are added. The mixture isheated to reflux for 3 hours.Work-up: The reaction mixture is poured on aqueous solution of EDTA,basified with saturated aqueous Na₂CO₃-solution and extracted withdiethyl ether. The crude4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidineis purified by column chromatography on silica gel (eluent: PE/EE=4:1).

Yield: brownish crystals; m.p.: 135-138° C. ¹H-NMR (CDCl₃): 1.49 (s, 9H,CH₃), 6.98 (d, 1H, H-5″, J_(5″6″)=5 Hz), 7.35-7.57 (m, 5H, phenyl), 8.03(d, 1H, H-6″), 9.00 (bs, 1H, NH).d)N-{4-[2-(2,2-Dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine

The4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidine(0.082 g, 0.17 mmol) is heated to reflux with aniline (0.032 g, 0.34mmol) and dry p-toluene sulfonic acid (0.026 g, 0.136 mmol) in drydioxane for five hours.Work-up: after cooling to room temperature the mixture is concentrateduntil nearly no solvent is present, poured into water, basified withsaturated aqueous Na₂CO₃-solution and extracted with ethyl acetate. Thecombined organic extracts are washed with brine, dried and the solventis evaporated. The crudeN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amineis purified by chromatography (silica gel, PE/EE 4:1)., yield the pureproduct as brownish crystals, having the m.p.: 290-292° C.

¹H-NMR (DMSO-d₆): 1.55 (s, 9H, CH₃), 6.42 (d, 1H, H-5″, J_(5″6″)=5 Hz),6.90 (t, 1H, H-4a, J_(4a3a)=10 Hz), 7.28 (t, 2H, H-3a, J_(2a3a)=10Hz),7.40-7.60 (m, 5H, phenyl), 7.73 (d, 2H, H-2a), 8.20 (d, 1H, H-6″), 9.60(s, 1H, NH), 11.79 (s, 1H, NHCO) ¹³C-NMR (DMSO-d₆): 27.8 (q, CH₃), 81.7(s, C(CH₃)₃), 107.8 (d), 118.8 (d), 121.4 (d), 124.9 (s), 128.4 (d, 2C),128.6 (d, 2C), 128.9 (d), 129.0 (d, 2C), 135.2 (s), 140.3 (s), 150.6(s), 152.8 (s), 157.8 (d), 158.6 (s), 159.6 (s), 160.6 (s)

e) TheN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine(0.12 g, 0.27 mmol) is suspended in 5 mL of dry CH₂Cl₂ and treated with5 equivalents of trifluoroacetic acid. The reaction mixture is stirredfor 12 hours at +25° C., then poured into water, basified with saturatedaqueous Na₂CO₃-solution and extracted with ethyl acetate. The combinedorganic extracts are concentrated to dryness and the last traces ofsolvent are evaporated in high vacuum.

Yield: pureN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine inform of yellow crystals of low solubility having a m.p. of 247-250° C.,¹H-NMR (DMSO-d₆): 6.25 (d, 1H, H-5″, J_(5″6″)=5 Hz), 6.92 (t, 1H, H-4a,J_(4a5a)=7 Hz), 7.25 (t, 2H, H-3a, J_(2a3a)=8 Hz), 7.40-7.53 (m, 5H,phenyl), 7.60 (s, 2H, NH₂), 7.73 (d, 2H, H-2a), 8.06 (d, 1H, H-6″), 9.45(s, 1H, NH). ¹³C-NMR (DMSO-d₆): 106.8 (d), 118.7 (d, 2C), 119.4 (s),121.2 (d), 128.3 (d, 2C), 128.5 (d), 128.7 (d, 2C), 128.9 (d, 2C), 135.9(s), 140.5 (s), 153.3 (s), 157.0 (d), 158.7 (s), 159.5 (s), 169.1 (s)

Synthesis Example 9N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-chloro-phenyl)-amine

a)N-{4-[2-(2,2-Dimethylethoxycarbonyl-amino)-4-(3-chloro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine

The4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidine(0.20 g, 0.416 mmol) is heated to reflux with 3-chloro-aniline (0.106 g,0.833 mmol) and dry p-toluene sulfonic acid (0.064 g, 0.33 mmol) in drydioxane for five hours.Work-up: after cooling to room temperature the mixture is concentrateduntil nearly no solvent is present, poured into water, basified withsaturated aqueous Na₂CO₃-solution and extracted with ethyl acetate. Thecombined organic extracts are washed with brine, dried and the solventis evaporated. The crudeN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-(3-chloro-phenyl)-thiazol-5-yl)]-pyrimidin-2-yl}-N-phenyl-amineis purified by chromatography (silica gel, PE/EE=2:1)., yield the pureproduct as yellow crystals, having the m.p.: 295-298° C.

¹H-NMR (DMSO-d_(6):) 1.52 (s, 9H, CH₃), 6.46 (d, 1H, H-5″, J_(5″6″)=5Hz), 6.97 (d, 1H, H-4a, J_(4a5a)=10 Hz), 7.29 (t, 1H, H-5a, J_(5a6a)=10Hz), 7.40-7.60 (m, 5H, phenyl), 7.63 (d, 1H, H-6a), 8.05 (s, 1H, H-2a),8.23 (d, 1H, H-6″), 9.85 (s, 1H, NH), 11.80 (s, 1H, NHCO) ¹³C-NMR(DMSO-d₆): 27.8 (q, CH₃), 81.7 (s, C(CH₃)₃), 108.2 (d), 117.0 (d), 117.9(d), 120.8 (d), 124.7 (s), 128.6 (d, 2C), 128.9 (d, 2C), 130.0 (d),133.0 (s), 135.1 (s), 141.9 (s), 150.9 (s), 152.8 (s), 157.8 (d), 158.7(s), 159.3 (s), 160.8 (s).

b) TheN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-(3-chloro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine(0.05 g, 0.11 mmol) is suspended in 5 mL of dry CH₂Cl₂ and treated with2 equivalents of trifluoroacetic acid. The reaction mixture is stirredfor 48 hours at +25° C., then poured into water, basified with saturatedaqueous Na₂CO₃-solution and extracted with ethyl acetate. The combinedorganic extracts are concentrated to dryness and the last traces ofsolvent are evaporated in high vacuum.

Yield: pureN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-chloro-phenyl)-aminein form of yellow crystals of low solubility having a m.p. of 243-245°C. ¹H-NMR (DMSO-d₆): 6.28 (d, 1H, H-5″, J_(5″6″)=5 Hz), 6.97 (d, 1H,H-4a, J_(4a5a)=7 Hz), 7.27 (t, 1H, H-5a, J_(5a6a)=8 Hz), 7.40-7.55 (m,5H, phenyl), 7.55-7.75 (m, 1H, H-6a), 7.65 (s, 2H, NH₂), 8.00 (t, 1H,H-2a, long-dist.-J=1 Hz), 8.10 (d, 1H, H-6″), 9.70 (s, 1H, NH)

Synthesis Example 10N-[4-(2-Amino4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-fluoro-phenyl)-amine

a)N-{4-[2-(2,2-Dimethylethoxycarbonyl-amino)-4-(3-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine

The4-[-2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidine(0.40 g, 0.83 mmol) is heated to reflux with 3-fluoro-aniline (0.185 g,1.66 mmol) and dry p-toluene sulfonic acid (0.127 g, 0.66 mmol) in drydioxane for four hours.Work-up: after cooling to room temperature the mixture is concentrateduntil nearly no solvent is present, poured into water, basified withsaturated aqueous Na₂CO₃-solution and extracted with ethyl acetate. Thecombined organic extracts are washed with brine, dried and the solventis evaporated. The crudeN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-(3-fluoro-phenyl)-thiazol-5-yl)]-pyrimidin-2-yl}-N-phenyl-amineis purified by chromatography (silica gel, PE/EE=2:1)., yield the pureproduct as brownish crystals, having the m.p.: 294-297° C. ¹H-NMR(DMSO-d₆): 1.52 (s, 9H, CH₃), 6.48 (d, 1H, H-5″, J_(5″6″)=5 Hz), 6.78(t, 1H, H-4a, J_(4a5a)=10 Hz, J_(4aF)=10 Hz), 7.30 (q, 1H, H-5a,J_(5a6a)=10 Hz, J_(5aF)=10 Hz), 7.40-7.60 (m, 6H, phenyl, H-6a), 7.82(dt, 1H, H-2a, J_(2aF)=14 Hz, long-dist.-J=2 Hz), 8.25 (d, 1H, H-6″),9.85 (s, 1H, NH), 11.80 (s, 1H, NHCO). ¹³C-NMR (DMSO-d₆): 27.8 (q, CH₃),81.7 (s, C(CH₃)₃), 105.2 (dd, C-2a, J_(2aF)=27 Hz), 107.5 (dd, C-4a,J_(4aF)=21 Hz), 108.3 (d), 114.4 (d, C-6a), 124.7 (s), 128.6 (d, 2C),129.0 (d, 2C), 129.7 (d), 129.9 (d), 135.1 (s), 142.2 (d, C-1a,J_(1aF)=11 Hz), 150.9 (s), 152.8 (s), 157.8 (d), 158.7 (s), 159.4 (s),160.8 (s), 162.3 (d, C-3a, J_(3aF)=240 Hz)b) TheN-{4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-(3-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine(0.05 g, 0.11 mmol) is suspended in 5 mL of dry CH₂Cl₂ and treated with5 equivalents of trifluoroacetic acid. The reaction mixture is stirredfor 12 hours at +25° C., then poured into water, basified with saturatedaqueous Na₂CO₃-solution and extracted with ethyl acetate. The combinedorganic extracts are concentrated to dryness and the last traces ofsolvent are evaporated in high vacuum.

Yield: pureN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-fluoro-phenyl)-aminein form of yellow crystals of low solubility having a m.p. of 243-245°C. ¹H-NMR (DMSO-d₆): 6.31 (d, 1H, H-5″, J_(5″6″)=5 Hz), 6.75 (t, 1H,H-4a, J_(4a5a)=8 Hz, J_(4aF)=8 Hz), 7.28 (q, 1H, H-5a, J_(5a6a)=8 Hz,J_(5aF)=8 Hz), 7.38-7.60 (m, 6H, phenyl, H-6a), 7.19 (s, 2H, NH₂), 7.83(d, 1H, H-2a, J_(2aF)=12 Hz), 8.12 (d, 1H, H-6″), 9.23 (s, 1H, NH)¹³C-NMR (DMSO-d₆): 105.1 (dd, J_(CF)=27 Hz), 107.3 (dd, J_(CF)=21 Hz),107.4 (d), 114.4 (d), 119.2 (s), 128.6 (d, 2C), 128.8 (d, C-4′), 128.9(d, 2C), 129.8 (dd, C-5a, J_(5aF)=10 Hz), 135.9 (s), 142.4 (d, C-1a,J_(1aF)=11 Hz), 153.7 (s), 157.0 (d), 158.8 (s), 159.3 (s), 162.4 (d,C-3a, J_(3aF)=240 Hz), 169.2 (s, C-2).

Synthesis Example 11N-[4-(2-Amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amine

The4-[2-(2,2-dimethylethoxycarbonyl-amino)-4-phenyl-thiazol-5-yl]-2-iodo-pyrimidine(1.0 g, 2.1 mmol) is heated to reflux with 3-methoxy-aniline (0.32 g,0.29 mL) and p-toluene sulfonic acid-mono hydrate (0.34 g, 1.8 mmol) indioxane for four hours.Work-up: when TLC-control indicates quantitative conversion (but still2-spots at R_(f)=0.23 and 0.09, PE/EE 2:1) and after cooling to roomtemperature the mixture is concentrated until nearly no solvent ispresent, poured into a mixture ethyl acetate and water, basified withsaturated aqueous Na₂CO₃-solution and extracted with ethyl acetate. Thecombined organic extracts are dried with Na₂SO₄ and the solvent isevaporated. 0.87 g of a brown residue remains. According to NMR-checkthis raw product contains about 67% of the desiredN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amineand a more polar product. The amount necessary for the NMR is easilysolved in CDCl₃ while larger quantities of are difficult to solve inCHCl₃, ethyl acetate or DMSO, whereby the desired title product resolveseasier than the main by-product. The raw product-mixture is digeratedwith a small quantity of CHCl₃ in order to separate it from the darklycolored impurities. The CHCl₃-phase which contains most of the titleproduct is decanted rapidly. 100 mg of the so-obtainedraw-product-mixture is stirred in 1 ml of TFA/CH₂Cl₂ (1:1) for 12 hours.Work-up: TLC control of the solution reveals only one spot atR_(f)=0.09. The reaction solution is transferred to a separation funnelwith ethyl acetate, neutralized with saturated aqueous NaHCO₃-solutionand extracted with ethyl acetate. The combined organic phase is driedwith Na₂SO₄ and the solvent is evaporated. The pureN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amineis obtained as yellow crystals in quantitative yield having a m.p. of115-117° C. ¹H-NMR (DMSO-d₆); 3.76 (s, 3H, CH₃), 6.24 (d, 1H, H-5″,J_(5″6″)=5 Hz), 6.52 (d, 1H, J=8 Hz), 7.14 (t, 1H, J=8 Hz), 7.29 (d, 1H,J=8 Hz), 7.40-7.55 (m, 6H, phenyl+1H), 7.63 (s, 2H, NH₂), 8.06 (d, 1H,H-6″), 8.10 (d, 1H, H-6″), 9.44 (s, 1H, NH).

Synthesis Example 12N-{4-[2-(4-Methylpiperazin-1-yl)-4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}]-N-phenyl-amine

a) 4-(2-Chloro-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine

To a suspension of copper-II-chloride (3.2 g, 23.5 mmol) andt-butylnitrite (2.9 g, 27.5 mmol) in acetonitrile (300 ml) is added4-(2-amino-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine (6.2 g,19.6 mmol) in small portions at room temperature. After stirring forthree hours at room temperature the reaction mixture is diluted withethyl acetate and washed repeatedly with water. Drying over magnesiumsulfate, filtering, evaporating the solvents and purification bychromatography gives the4-(2-chloro-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine as ayellow colored solid.b)4-[2-(4-Methylpiperazin-1-yl)-4-phenyl-thiazol-5-yl]-2-methylsulfinyl-pyrimidine

A solution of N-methylpiperazine (0.6 g, 6.0 mmol) in tetrahydrofuran (5ml) is added to a well stirred solution of4-(2-chloro-4-phenyl-thiazol-5-yl)-2-methylsulfinyl-pyrimidine (1.0g,3.0 mmol) in tetrahydrofuran (20 ml) at +5° C. The reaction mixture isallowed to warm to room temperature over night. Evaporation of thesolvent leaves a crystalline residue that is suspended in water,filtered with suction, washed with diethyl ether and dried under vacuum.The product4-[2-(4-methylpiperazin-1-yl)-4-phenyl-thiazol-5-yl]-2-methylsulfinyl-pyrimidineshows a m.p. of 166-169° C.c) A mixture of4-[2-(4-methylpiperazin-1-yl)-4-phenyl-thiazol-5-yl]-2-methylsulfinyl-pyrimidine(0.5 g, 1.25 mmol) and aniline (1.5 g, 15.8mmol) is heated at +100° C.After the addition of boron trifluoride diethyl etherate (3 drops) thesolution is heated at +150° C. for half an hour. After the reactionmixture is cooled to room temperature water and diethylether is addedsequentially to precipitate the product. The crystals are filtered andwashed thoroughly with diethyl ether to give theN-{4-[2-(4-methylpiperazin-1-yl)4-phenyl-thiazol-5-yl]-pyrimidin-2-yl}]-N-phenyl-aminein pure form, having a m.p. of 239-240° C.

Using analogous procedures to the above described working examples thecompounds of the following tables may be obtained. TABLE 01 Compounds ofthe general structure I.01, wherein each individual species correspondsto the combination of the definitions R₁, R₂, R₃, R₄, R₅, und R₆ of thelines of table A. (I.01)

TABLE 02 Compounds of the general structure I.02, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.02)

TABLE 03 Compounds of the general structure I.03, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.03)

TABLE 04 Compounds of the general structure I.04, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.04)

TABLE 05 Compounds of the general structure I.05, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.05)

TABLE 06 Compounds of the general structure I.06, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.06)

TABLE 07 Compounds of the general structure I.07, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, and R₆ of the lines of table A.

(I.07)

TABLE 08 Compounds of the general structure I.08, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.08)

TABLE 09 Compounds of the general structure I.09, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.09)

TABLE 10 Compounds of the general structure I.10, wherein eachindividual species corresponds to the combination of the definitions R₁,R₂, R₃, R₄, R₅, und R₆ of the lines of table A. (I.10)

TABLE A Comp- No. R₁ R₂ R₃ R₄ R₅ R₆ 0001 H H H —CH₂—O—CH₃ H H 0002 H H H—NH—CO—CH₃ H H 0003 H H H —CH₂—NH—CO—CH₃ H H 0004 H H H—CH(CH₃)—NH—CO—CH₃ H H 0005 H H H —C(CH₃)₂—NH—CO—CH₃ H H 0006 H H H—CH(CH₃)—O—CH₃ H H 0007 H H H —C(CH₃)₂—O—CH₃ H H 0008 H H H—CH(CH₃)—O—CO—CH₃ H H 0009 H H H —CH₂—O—CO—CH₃ H H 0010 H H H—C(CH₃)₂—O—CO—CH₃ H H 0011 H H H —CH₂—CH₂—O—H H H 0012 H H H—CH₂—CH₂—O—CH₃ H H 0013 H H H

H H 0014 H H H

H H 0015 H H H

H H 0016 H H H

H H 0017 H H H

H H 0018 H H H

H H 0019 H H H

H H 0020 H H H

H H 0021 H H H

H H 0022 H H H

H H 0023 H H H

H H 0024 H H H

H H 0025 H H H H H H 0026 H H H CN H H 0027 H H H —C(CH₃)₂—OH H H 0028 HH H —CH₂—OH H H 0029 H H H —CO—CH₃ H H 0030 H H H —C(═NOH)—CH₃ H H 0031H H H —CH(OH)—CH₃ H H 0032 H H H (3) —CO—O—CH₂— (4) H 0033 H H H —CH₂—CNH H 0034 H H H —C(═NO—CH₃)—CH₃ H H 0035 H H H —CO—O—CH₃ H H 0036 H H H—NH—CO—C₃H₅-cycl. H H 0037 H H H —CO—CH₃ Cl H 0038 H H H —OH H H 0039 HH H —OH —OCH₃ H 0040 H H H —OCH₃ H —OCH₃ 0041 H H H —SCH₃ H H 0042 H H H—OCH₃ H H 0043 H H H —OCH₃ —OCH₃ —OCH₃ 0044 H H H —OH —OCH₃ —OCH₃ 0045 HH H H —SCH₃ H 0046 H H —OCH₃ H —OCH₃ H 0047 H H H —OCH₃ —OH H 0048 H H—OCH₃ H H H 0049 H H H —CH₂—CH₃ H H 0050 H H —OCH₃ —CH(CH₃)₂ H H 0051 HH H —C₃H₇-n H H 0052 H H H —OCH₂—CH₃ H H 0053 H H H Cl H H 0054 H H H BrH H 0055 H H H Cl Cl H 0056 H H H OH OH OH 0057 H H Cl Cl H Cl 0058 H HH —CF₃ H H 0059 H H H —OCF₃ H H 0060 H H H —C₂F₅ H H 0061 H H H—C₄H₉-tert H H 0062 H H H —OC₃H₇-i H H 0063 H H H CH₃ H H 0064 H H H—SO₂—CH₃ H H 0065 H H H —NH—CH₂—CH₃ H H 0066 H H H —O—CH₂—CH═CH₂ H H0067 H H H —O—CH₂—C═CH H H 0068 H H H —NH—CH₂—CH₂—NH—CH₃ H H 0069 H H H—SO₂—C₂H₅ H H 0070 H H H —SO₂—CH₃ Cl H 0071 C₂H₅ H H —CH₂—O—CH₃ H H 0072C₂H₅ H H —NH—CO—CH₃ H H 0073 C₂H₅ H H —CH₂—NH—CO—CH₃ H H 0074 C₂H₅ H H—CH(CH₃)—NH—CO—CH₃ H H 0075 C₂H₅ H H —C(CH₃)₂—NH—CO—CH₃ H H 0076 C₂H₅ HH —CH(CH₃)—O—CH₃ H H 0077 C₂H₅ H H —C(CH₃)₂—O—CH₃ H H 0078 C₂H₅ H H—CH(CH₃)—O—CO—CH₃ H H 0079 C₂H₅ H H —CH₂—O—CO—CH₃ H H 0080 C₂H₅ H H—C(CH₃)₂—O—CO—CH₃ H H 0081 C₂H₅ H H —CH₂—CH₂—O—H H H 0082 C₂H₅ H H—CH₂—CH₂—O—CH₃ H H 0083 C₂H₅ H H

H H 0084 C₂H₅ H H

H H 0085 C₂H₅ H H

H H 0086 C₂H₅ H H

H H 0087 C₂H₅ H H

H H 0088 C₂H₅ H H

H H 0089 C₂H₅ H H

H H 0090 C₂H₅ H H

H H 0091 C₂H₅ H H

H H 0092 C₂H₅ H H

H H 0093 C₂H₅ H H

H H 0094 C₂H₅ H H

H H 0095 C₂H₅ H H H H H 0096 C₂H₅ H H CN H H 0097 C₂H₅ H H —C(CH₃)₂—OH HH 0098 C₂H₅ H H —CH₂—OH H H 0099 C₂H₅ H H —CO—CH₃ H H 0100 C₂H₅ H H—C(═NOH)—CH₃ H H 0101 C₂H₅ H H —CH(OH)—CH₃ H H 0102 C₂H₅ H H (3)—CO—O—CH₂— (4) H 0103 C₂H₅ H H —CH₂—O—CO—CH₃ H H 0104 C₂H₅ H H—C(═NO—CH₃)—CH₃ H H 0105 C₂H₅ H H —CO—O—CH₃ H H 0106 C₂H₅ H H—NH—CO—C₃H₅-cycl. H H 0107 C₂H₅ H H —CO—CH₃ Cl H 0108 C₂H₅ H H —OH H H0109 C₂H₅ H H —OH —OCH₃ H 0110 C₂H₅ H H —OCH₃ H —OCH₃ 0111 C₂H₅ H H—SCH₃ H H 0112 C₂H₅ H H —OCH₃ H H 0113 C₂H₅ H H —OCH₃ —OCH₃ —OCH₃ 0114C₂H₅ H H —OH —OCH₃ —OCH₃ 0115 C₂H₅ H H H —SCH₃ H 0116 C₂H₅ H H H —OCH₃ H0117 C₂H₅ H H —OCH₃ —OH H 0118 C₂H₅ H —OCH₃ —CH₃ H H 0119 C₂H₅ H H—CH₂—CH₃ H H 0120 C₂H₅ H —OCH₃ —CH(CH₃)₂ H H 0121 C₂H₅ H H —C₃H₇-n H H0122 C₂H₅ H H —OCH₂—CH₃ H H 0123 C₂H₅ H H F H H 0124 C₂H₅ H H Cl H H0125 C₂H₅ H H Br H H 0126 C₂H₅ H H Cl Cl H 0127 C₂H₅ H H OH OH OH 0128C₂H₅ H Cl Cl H Cl 0129 C₂H₅ H H —CF₃ H H 0130 C₂H₅ H H —OCF₃ H H 0131C₂H₅ H H —C₂F₅ H H 0132 C₂H₅ H H —C₄H₉-tert H H 0133 C₂H₅ H H —OC₃H₇-i HH 0134 C₂H₅ H H —SO—C₃ H H 0135 C₂H₅ H H —SO₂—CH₃ H H 0136 C₂H₅ H H—NH—CH₂—CH₃ H H 0137 C₂H₅ H H —O—CH₂—CH═CH₂ H H 0138 C₂H₅ H H—O—CH₂—C═CH H H 0139 C₂H₅ H H —NH—CH₂—CH₂—NH—CH₃ H H 0140 C₂H₅ H H—SO₂—C₂H₅ H H 0141 C₂H₅ H H —SO₂—CH₃ Cl H 0142 CH₃ H H —CH₂—O—CH₃ H H0143 CH₃ H H —NH—CO—CH₃ H H 0144 CH₃ H H —CH₂—NH—CO—CH₃ H H 0145 CH₃ H H—CH(CH₃)—NH—CO—CH₃ H H 0146 CH₃ H H —C(CH₃)₂—NH—CO—CH₃ H H 0147 CH₃ H H—CH(CH₃)—O—CH₃ H H 0148 CH₃ H H —C(CH₃)₂—O—CH₃ H H 0149 CH₃ H H—CH(CH₃)—O—CO—CH₃ H H 0150 CH₃ H H —CH₂—O—CO—CH₃ H H 0151 CH₃ H H—C(CH₃)₂—O—CO—CH₃ H H 0152 CH₃ H H —CH₂—CH₂—O—H H H 0153 CH₃ H H

H H 0154 CH₃ H H

H H 0155 CH₃ H H

H H 0156 CH₃ H H

H H 0157 CH₃ H H

H H 0158 CH₃ H H

H H 0159 CH₃ H H

H H 0160 CH₃ H H

H H 0161 CH₃ H H

H H 0162 CH₃ H H

H H 0163 CH₃ H H

H H 0164 CH₃ H H

H H 0165 CH₃ H H H H H 0166 CH₃ H H CN H H 0167 CH₃ H H —C(CH₃)₂—OH H H0168 CH₃ H H —CH₂—OH H H 0169 CH₃ H H —CO—CH₃ H H 0170 CH₃ H H—C(═NOH)—CH₃ H H 0171 CH₃ H H —CH(OH)—CH₃ H H 0172 CH₃ H H (3)—CO—O—CH₂— (4) H 0173 CH₃ H H —CH₂—O—CO—CH₃ H H 0174 CH₃ H H—C(═NO—CH₃)—CH₃ H H 0175 CH₃ H H —CO—O—CH₃ H H 0176 CH₃ H H—NH—CO—C₃H₅-cycl. H H 0177 CH₃ H H —CO—CH₃ Cl H 0178 CH₃ H H —OH H H0179 CH₃ H H —OH —OCH₃ H 0180 CH₃ H H —OCH₃ H —OCH₃ 0181 CH₃ H H —SCH₃ HH 0182 CH₃ H H —OCH₃ H H 0183 CH₃ H H —OCH₃ —OCH₃ —OCH₃ 0184 CH₃ H H —OH—OCH₃ —OCH₃ 0185 CH₃ H H H —SCH₃ H 0186 CH₃ H H H —OCH₃ H 0187 CH₃ H H—OCH₃ —OH H 0188 CH₃ H —OCH₃ —CH₃ H H 0189 CH₃ H H —CH₂—CH₃ H H 0190 CH₃H —OCH₃ —CH(CH₃)₂ H H 0191 CH₃ H H —C₃H₇-n H H 0192 CH₃ H H —OCH₂—CH₃ HH 0193 CH₃ H H F H H 0194 CH₃ H H Cl H H 0195 CH₃ H H Br H H 0196 CH₃ HH Cl Cl H 0197 CH₃ H H OH OH OH 0198 CH₃ H Cl Cl H Cl 0199 CH₃ H H —CF₃H H 0200 H H H —OCH₂—CF₃ H H 0201 CH₃ H H —C₂F₅ H H 0202 CH₃ H H—C₄H₉-tert H H 0203 CH₃ H H —OC₃H₇-i H H 0204 CH₃ H H —SO—CH₃ H H 0205CH₃ H H —SO₂—CH₃ H H 0206 CH₃ H H —NH—CH₂—CH₃ H H 0207 CH₃ H H—O—CH₂—CH═CH₂ H H 0208 CH₃ H H —O—CH₂—C═CH H H 0209 CH₃ H H—NH—CH₂—CH₂—NH—CH₃ H H 0210 CH₃ H H —SO₂—C₂H₅ H H 0211 CH₃ H H —SO₂—CH₃Cl H 0212 CH₃ CH₃ H —CH₂—O—CH₃ H H 0213 CH₃ CH₃ H —NH—CO—CH₃ H H 0214CH₃ CH₃ H —CH₂—NH—CO—CH₃ H H 0215 CH₃ CH₃ H —CH(CH₃)—NH—CO—CH₃ H H 0216CH₃ CH₃ H —C(CH₃)₂—NH—CO—CH₃ H H 0217 CH₃ CH₃ H —CH(CH₃)—O—CH₃ H H 0218CH₃ CH₃ H —C(CH₃)₂—O—CH₃ H H 0219 CH₃ CH₃ H —CH(CH₃)—O—CO—CH₃ H H 0220CH₃ CH₃ H —CH₂—O—CO—CH₃ H H 0221 CH₃ CH₃ H —C(CH₃)₂—O—CO—CH₃ H H 0222CH₃ CH₃ H —CH₂—CH₂—O—H H H 0223 CH₃ CH₃ H —CH₂—CH₂—O—CH₃ H H 0224 CH₃CH₃ H

H H 0225 CH₃ CH₃ H

H H 0226 CH₃ CH₃ H

H H 0227 CH₃ CH₃ H

H H 0228 CH₃ CH₃ H

H H 0229 CH₃ CH₃ H

H H 0230 CH₃ CH₃ H

H H 0231 CH₃ CH₃ H

H H 0232 CH₃ CH₃ H

H H 0233 CH₃ CH₃ H

H H 0234 CH₃ CH₃ H

H H 0235 CH₃ CH₃ H

H H 0236 CH₃ CH₃ H H H H 0237 CH₃ CH₃ H CN H H 0238 CH₃ CH₃ H—C(CH₃)₂—OH H H 0239 CH₃ CH₃ H —CH₂—OH H H 0240 CH₃ CH₃ H —CO—CH₃ H H0241 CH₃ CH₃ H —C(═NOH)—CH₃ H H 0242 CH₃ CH₃ H —CH(OH)—CH₃ H H 0243 CH₃CH₃ H (3) —CO—O—CH₂— (4) H 0244 CH₃ CH₃ H —CH₂—O—CO—CH₃ H H 0245 CH₃ CH₃H —C(═NO—CH₃)—CH₃ H H 0246 CH₃ CH₃ H —CO—O—CH₃ H H 0247 CH₃ CH₃ H—NH—CO—C₃H₅-cycl. H H 0248 CH₃ CH₃ H —NH—CO—C₆H₁₁-cycl. H H 0249 CH₃ CH₃H —CO—CH₃ Cl H 0250 CH₃ CH₃ H —OH H H 0251 CH₃ CH₃ H —OH —OCH₃ H 0252CH₃ CH₃ H —OCH₃ H —OCH₃ 0253 CH₃ CH₃ H —OCH₃ H H 0254 CH₃ CH₃ H —OCH₃—OCH₃ —OCH₃ 0255 CH₃ CH₃ H —OH —OCH₃ —OCH₃ 0256 CH₃ CH₃ H H —SCH₃ H 0257CH₃ CH₃ H H —OCH₃ H 0258 CH₃ CH₃ H —OCH₃ —OH H 0259 CH₃ CH₃ —OCH₃ —CH₃ HH 0260 CH₃ CH₃ H —CH₂—CH₃ H H 0261 CH₃ CH₃ —OCH₃ —CH(CH₃)₂ H H 0262 CH₃CH₃ H —C₃H₇-n H H 0263 CH₃ CH₃ H —OCH₂—CH₃ H H 0264 CH₃ CH₃ H F H H 0265CH₃ CH₃ H Cl H H 0266 CH₃ CH₃ H Br H H 0267 CH₃ CH₃ H Cl Cl H 0268 CH₃CH₃ H OH OH OH 0269 CH₃ CH₃ Cl Cl H Cl 0270 CH₃ CH₃ H —CF₃ H H 0271 CH₃CH₃ H —OCF₃ H H 0272 CH₃ CH₃ H —C₂F₅ H H 0273 CH₃ CH₃ H —C₄H₉-tert H H0274 CH₃ CH₃ H —OC₃H₇-i H H 0275 CH₃ CH₃ H —SO—CH₃ H H 0276 CH₃ CH₃ H—SO₂—CH₃ H H 0277 CH₃ CH₃ H —NH—CH₂—CH₃ H H 0278 CH₃ CH₃ H —O—CH₂—CH═CH₂H H 0279 CH₃ CH₃ H —O—CH₂—C═CH H H 0280 CH₃ CH₃ H —NH—CH₂—CH₂—NH—CH₃ H H0281 CH₃ CH₃ H —SO₂—C₂H₅ H H 0282 CH₃ CH₃ H —SO₂—CH₃ Cl H 0283 —CO—CH₃ HH —CH₂—O—CH₃ H H 0284 —CO—CH₃ H H —NH—CO—CH₃ H H 0285 —CO—CH₃ H H—CH₂—NH—CO—CH₃ H H 0286 —CO—CH₃ H H —CH(CH₃)—NH—CO—CH₃ H H 0287 —CO—CH₃H H —C(CH₃)₂—NH—CO—CH₃ H H 0288 —CO—CH₃ H H —CH(CH₃)—O—CH₃ H H 0289—CO—CH₃ H H —C(CH₃)₂—O—CH₃ H H 0290 —CO—CH₃ H H —CH(CH₃)—O—CO—CH₃ H H0291 —CO—CH₃ H H —CH₂—O—CO—CH₃ H H 0292 —CO—CH₃ H H —C(CH₃)₂—O—CO—CH₃ HH 0293 —CO—CH₃ H H —CH₂—CH₂—O—H H H 0294 —CO—CH₃ H H —CH₂—CH₂—O—CH₃ H H0295 —CO—CH₃ H H

H H 0296 —CO—CH₃ H H

H H 0297 —CO—CH₃ H H

H H 0298 —CO—CH₃ H H

H H 0299 —CO—CH₃ H H

H H 0300 —CO—CH₃ H H

H H 0301 —CO—CH₃ H H

H H 0302 —CO—CH₃ H H

H H 0303 —CO—CH₃ H H

H H 0304 —CO—CH₃ H H

H H 0305 —CO—CH₃ H H

H H 0306 —CO—CH₃ H H

H H 0307 —CO—CH₃ H H H H H 0308 —CO—CH₃ H H CN H H 0309 —CO—CH₃ H H—C(CH₃)₂—OH H H 0310 —CO—CH₃ H H —CH₂—OH H H 0311 —CO—CH₃ H H —CO—CH₃ HH 0312 —CO—CH₃ H H —C(═NOH)—CH₃ H H 0313 —CO—CH₃ H H —CH(OH)—CH₃ H H0314 —CO—CH₃ H H (3) —CO—O—CH₂— (4) H 0315 —CO—CH₃ H H —CH₂—O—CO—CH₃ H H0316 —CO—CH₃ H H —C(═NO—CH₃)—CH₃ H H 0317 —CO—CH₃ H H —CO—O—CH₃ H H 0318—CO—CH₃ H H —NH—CO—C₃H₅-cycl. H H 0319 —CO—CH₃ H H —CO—CH₃ Cl H 0320—CO—CH₃ H H —OH H H 0321 —CO—CH₃ H H —OH —OCH₃ H 0322 —CO—CH₃ H H —OCH₃H —OCH₃ 0323 —CO—CH₃ H H —SCH₃ H H 0324 —CO—CH₃ H H —OCH₃ H H 0325—CO—CH₃ H H —OCH₃ —OCH₃ —OCH₃ 0326 —CO—CH₃ H H —OH —OCH₃ —OCH₃ 0327—CO—CH₃ H H H —SCH₃ H 0328 —CO—CH₃ H H H —OCH₃ H 0329 —CO—CH₃ H H —OCH₃—OH H 0330 —CO—CH₃ H —OCH₃ —CH₃ H H 0331 —CO—CH₃ H H —CH₂—CH₃ H H 0332—CO—CH₃ H —OCH₃ —CH(CH₃)₂ H H 0333 —CO—CH₃ H H —C₃H₇-n H H 0334 —CO—CH₃H H —OCH₂—CH₃ H H 0335 —CO—CH₃ H H F H H 0336 —CO—CH₃ H H Cl H H 0337—CO—CH₃ H H Br H H 0338 —CO—CH₃ H H Cl Cl H 0339 —CO—CH₃ H H OH OH OH0340 —CO—CH₃ H Cl Cl H Cl 0341 —CO—CH₃ H H —CF₃ H H 0342 —CO—CH₃ H H—OCF₃ H H 0343 —CO—CH₃ H H —C₂F₅ H H 0344 —CO—CH₃ H H —C₄H₉-tert H H0345 —CO—CH₃ H H —OC₃H₇-i H H 0346 —CO—CH₃ H H —SO—CH₃ H H 0347 —CO—CH₃H H —SO₂—CH₃ H H 0348 —CO—CH₃ H H —NH—CH₂—CH₃ H H 0349 —CO—CH₃ H H—O—CH₂—CH═CH₂ H H 0350 —CO—CH₃ H H —O—CH₂—C═CH H H 0351 —CO—CH₃ H H—NH—CH₂—CH₂—NH —CH₃ H H 0352 —CO—CH₃ H H —SO₂—C₂H₅ H H 0353 —CO—C₂H₅ H H—CH₂—O—CH₃ H H 0354 —CO—C₂H₅ H H —NH—CO—CH₃ H H 0355 —CO—C₂H₅ H H—CH₂—NH—CO—CH₃ H H 0356 —CO—C₂H₅ H H —CH(CH₃)—NH—CO—CH₃ H H 0357—CO—C₂H₅ H H —C(CH₃)₂—NH—CO—CH₃ H H 0358 —CO—C₂H₅ H H —CH(CH₃)—O—CH₃ H H0359 —CO—C₂H₅ H H —C(CH₃)₂—O—CH₃ H H 0360 —CO—C₂H₅ H H —CH(CH₃)—O—CO—CH₃H H 0361 —CO—C₂H₅ H H —CH₂—O—CO—CH₃ H H 0362 —CO—C₂H₅ H H—C(CH₃)₂—O—CO—CH₃ H H 0363 —CO—C₂H₅ H H —CH₂—CH₂—O—H H H 0364 —CO—C₂H₅ HH —CH₂—CH₂—O—CH₃ H H 0365 —CO—C₂H₅ H H

H H 0366 —CO—C₂H₅ H H

H H 0367 —CO—C₂H₅ H H

H H 0368 —CO—C₂H₅ H H

H H 0369 —CO—C₂H₅ H H

H H 0370 —CO—C₂H₅ H H

H H 0371 —CO—C₂H₅ H H

H H 0372 —CO—C₂H₅ H H

H H 0373 —CO—C₂H₅ H H

H H 0374 —CO—C₂H₅ H H

H H 0375 —CO—C₂H₅ H H

H H 0376 —CO—C₂H₅ H H

H H 0377 —CO—C₂H₅ H H H H H 0378 —CO—C₂H₅ H H CN H H 0379 —CO—C₂H₅ H H—C(CH₃)₂—OH H H 0380 —CO—C₂H₅ H H —CH₂—OH H H 0381 —CO—C₂H₅ H H —CO—CH₃H H 0382 —CO—C₂H₅ H H —C(═NOH)—CH₃ H H 0383 —CO—C₂H₅ H H —CH(OH)—CH₃ H H0384 —CO—C₂H₅ H H (3) —CO—O—CH₂— (4) H 0385 —CO—C₂H₅ H H —CH₂—O—CO—CH₃ HH 0386 —CO—C₂H₅ H H —C(═NO—CH₃)—CH₃ H H 0387 —CO—C₂H₅ H H —CO—O—CH₃ H H0388 —CO—C₂H₅ H H —NH—CO—C₃H₅-cycl. H H 0389 —CO—C₂H₅ H H —CO—CH₃ Cl H0390 —CO—C₂H₅ H H —OH H H 0391 —CO—C₂H₅ H H —OH —OCH₃ H 0392 —CO—C₂H₅ HH —OCH₃ H —OCH₃ 0393 —CO—C₂H₅ H H —SCH₃ H H 0394 —CO—C₂H₅ H H —OCH₃ H H0395 —CO—C₂H₅ H H —OCH₃ —OCH₃ —OCH₃ 0396 —CO—C₂H₅ H H —OH —OCH₃ —OCH₃0397 —CO—C₂H₅ H H H —SCH₃ H 0398 —CO—C₂H₅ H H H —OCH₃ H 0399 —CO—C₂H₅ HH —OCH₃ —OH H 0400 —CO—C₂H₅ H —OCH₃ —CH₃ H H 0401 —CO—C₂H₅ H H —CH₂—CH₃H H 0402 —CO—C₂H₅ H —OCH₃ —CH(CH₃)₂ H H 0403 —CO—C₂H₅ H H —C₃H₇-n H H0404 —CO—C₂H₅ H H —OCH₂—CH₃ H H 0405 —CO—C₂H₅ H H F H H 0406 —CO—C₂H₅ HH Cl H H 0407 —CO—C₂H₅ H H Br H H 0408 —CO—C₂H₅ H H Cl Cl H 0409—CO—C₂H₅ H H OH OH OH 0410 —CO—C₂H₅ H Cl Cl H Cl 0411 —CO—C₂H₅ H H —CF₃H H 0412 —CO—C₂H₅ H H —OCF₃ H H 0413 —CO—C₂H₅ H H —C₂F₅ H H 0414—CO—C₂H₅ H H —C₄H₉-tert H H 0415 —CO—C₂H₅ H H —OC₃H₇-i H H 0416 —CO—C₂H₅H H —SO—CH₃ H H 0417 —CO—C₂H₅ H H —SO₂—CH₃ H H 0418 —CO—C₂H₅ H H—NH—CH₂—CH₃ H H 0419 —CO—C₂H₅ H H —O—CH₂—CH═CH₂ H H 0420 —CO—C₂H₅ H H—O—CH₂—C═CH H H 0421 —CO—C₂H₅ H H —NH—CH₂—CH₂—NH—CH₃ H H 0422 —CO—C₂H₅ HH —SO₂—C₂H₅ H H 0423 —CO—C₂H₅ H H —SO₂—CH₃ Cl H 0424 —CO—CH(CH₃)—C₂H₅ HH —CH₂—O—CH₃ H H 0425 —CO—CH(CH₃)—C₂H₅ H H —NH—CO—CH₃ H H 0426—CO—CH(CH₃)—C₂H₅ H H —CH₂—NH—CO—CH₃ H H 0427 —CO—CH(CH₃)—C₂H₅ H H—CH(CH₃)—NH—CO—CH₃ H H 0428 —CO—CH(CH₃)—C₂H₅ H H —C(CH₃)₂—NH—CO—CH₃ H H0429 —CO—CH(CH₃)—C₂H₅ H H —CH(CH₃)—O—CH₃ H H 0430 —CO—CH(CH₃)—C₂H₅ H H—C(CH₃)₂—O—CH₃ H H 0431 —CO—CH(CH₃)—C₂H₅ H H —CH(CH₃)—O—CO—CH₃ H H 0432—CO—CH(CH₃)—C₂H₅ H H —CH₂—O—CO—CH₃ H H 0433 —CO—CH(CH₃)—C₂H₅ H H—C(CH₃)₂—O—CO—CH₃ H H 0434 —CO—CH(CH₃)—C₂H₅ H H —CH₂—CH₂—O—H H H 0435—CO—CH(CH₃)—C₂H₅ H H —CH₂—CH₂—O—CH₃ H H 0436 —CO—CH(CH₃)—C₂H₅ H H

H H 0437 —CO—CH(CH₃)—C₂H₅ H H

H H 0438 —CO—CH(CH₃)—C₂H₅ H H

H H 0439 —CO—CH(CH₃)—C₂H₅ H H

H H 0440 —CO—CH(CH₃)—C₂H₅ H H

H H 0441 —CO—CH(CH₃)—C₂H₅ H H

H H 0442 —CO—CH(CH₃)—C₂H₅ H H

H H 0443 —CO—CH(CH₃)—C₂H₅ H H

H H 0444 —CO—CH(CH₃)—C₂H₅ H H

H H 0445 —CO—CH(CH₃)—C₂H₅ H H

H H 0446 —CO—CH(CH₃)—C₂H₅ H H

H H 0447 —CO—CH(CH₃)—C₂H₅ H H

H H 0448 —CO—CH(CH₃)—C₂H₅ H H H H H 0449 —CO—CH(CH₃)—C₂H₅ H H CN H H0450 —CO—CH(CH₃)—C₂H₅ H H —C(CH₃)₂—OH H H 0451 —CO—CH(CH₃)—C₂H₅ H H—CH₂—OH H H 0452 —CO—CH(CH₃)—C₂H₅ H H —CO—CH₃ H H 0453 —CO—CH(CH₃)—C₂H₅H H —CH(OH)—CH₃ H H 0454 —CO—CH(CH₃)—C₂H₅ H H (3) —CO—O—CH₂— (4) H 0455—CO—CH(CH₃)—C₂H₅ H H —CH₂—O—CO—CH₃ H H 0456 —CO—CH(CH₃)—C₂H₅ H H—C(═NO—CH₃)—CH₃ H H 0457 —CO—CH(CH₃)—C₂H₅ H H —CO—O—CH₃ H H 0458—CO—CH(CH₃)—C₂H₅ H H —NH—CO—C₃H₅-cycl. H H 0459 —CO—CH(CH₃)—C₂H₅ H H—CO—CH₃ Cl H 0460 —CO—CH(CH₃)—C₂H₅ H H —OH H H 0461 —CO—CH(CH₃)—C₂H₅ H H—OH —OCH₃ H 0462 —CO—CH(CH₃)—C₂H₅ H H —OCH₃ H —OCH₃ 0463—CO—CH(CH₃)—C₂H₅ H H —SCH₃ H H 0464 —CO—CH(CH₃)—C₂H₅ H H —OCH₃ H H 0465—CO—CH(CH₃)—C₂H₅ H H —OCH₃ —OCH₃ —OCH₃ 0466 —CO—CH(CH₃)—C₂H₅ H H —OH—OCH₃ —OCH₃ 0467 —CO—CH(CH₃)—C₂H₅ H H H —SCH₃ H 0468 —CO—CH(CH₃)—C₂H₅ HH H —OCH₃ H 0469 —CO—CH(CH₃)—C₂H₅ H H —OCH₃ —OH H 0470 —CO—CH(CH₃)—C₂H₅H —OCH₃ —CH₃ H H 0471 —CO—CH(CH₃)—C₂H₅ H H —CH₂—CH₃ H H 0472—CO—CH(CH₃)—C₂H₅ H —OCH₃ —CH(CH₃)₂ H H 0473 —CO—CH(CH₃)—C₂H₅ H H —C₃H₇-nH H 0474 —CO—CH(CH₃)—C₂H₅ H H —OCH₂—CH₃ H H 0475 —CO—CH(CH₃)—C₂H₅ H H FH H 0476 —CO—CH(CH₃)—C₂H₅ H H Cl H H 0477 —CO—CH(CH₃)—C₂H₅ H H Br H H0478 —CO—CH(CH₃)—C₂H₅ H H Cl Cl H 0479 —CO—CH(CH₃)—C₂H₅ H H OH OH OH0480 —CO—CH(CH₃)—C₂H₅ H Cl Cl H Cl 0481 —CO—CH(CH₃)—C₂H₅ H H —CF₃ H H0482 —CO—CH(CH₃)—C₂H₅ H H —OCF₃ H H 0483 —CO—CH(CH₃)—C₂H₅ H H —C₂F₅ H H0484 —CO—CH(CH₃)—C₂H₅ H H —C₄H₉-tert H H 0485 —CO—CH(CH₃)—C₂H₅ H H—OC₃H₇-i H H 0486 —CO—CH(CH₃)—C₂H₅ H H —SO—CH₃ H H 0487 —CO—CH(CH₃)—C₂H₅H H —SO₂—CH₃ H H 0488 —CO—CH(CH₃)—C₂H₅ H H —NH—CH₂—CH₃ H H 0489—CO—CH(CH₃)—C₂H₅ H H —O—CH₂—CH═CH₂ H H 0490 —CO—CH(CH₃)—C₂H₅ H H—O—CH₂—C═CH H H 0491 —CO—CH(CH₃)—C₂H₅ H H —NH—CH₂—CH₂—NH—CH₃ H H 0492—CO—CH(CH₃)—C₂H₅ H H —SO₂—C₂H₅ H H 0493 —CO—CH(CH₃)—C₂H₅ H H —SO₂—CH₃ ClH 0494 —CO—C₃F₇-n H H —CH₂—O—CH₃ H H 0495 —CO—C₃F₇-n H H —NH—CO—CH₃ H H0496 —CO—C₃F₇-n H H —CH₂—NH—CO—CH₃ H H 0497 —CO—C₃F₇-n H H—CH(CH₃)—NH—CO—CH₃ H H 0498 —CO—C₃F₇-n H H —C(CH₃)₂—NH—CO—CH₃ H H 0499—CO—C₃F₇-n H H —CH(CH₃)—O—CH₃ H H 0500 —CO—C₃F₇-n H H —C(CH₃)₂—O—CH₃ H H0501 —CO—C₃F₇-n H H —CH(CH₃)—O—CO—CH₃ H H 0502 —CO—C₃F₇-n H H—CH₂—O—CO—CH₃ H H 0503 —CO—C₃F₇-n H H —C(CH₃)₂—O—CO—CH₃ H H 0504—CO—C₃F₇-n H H —CH₂—CH₂—O—H H H 0505 —CO—C₃F₇-n H H —CH₂—CH₂—O—CH₃ H H0506 —CO—C₃F₇-n H H

H H 0507 —CO—C₃F₇-n H H

H H 0508 —CO—C₃F₇-n H H

H H 0509 —CO—C₃F₇-n H H

H H 0510 —CO—C₃F₇-n H H

H H 0511 —CO—C₃F₇-n H H

H H 0512 —CO—C₃F₇-n H H

H H 0513 —CO—C₃F₇-n H H

H H 0514 —CO—C₃F₇-n H H

H H 0515 —CO—C₃F₇-n H H

H H 0516 —CO—C₃F₇-n H H

H H 0517 —CO—C₃F₇-n H H

H H 0518 —CO—C₃F₇-n H H H H H 0519 —CO—C₃F₇-n H H CN H H 0520 —CO—C₃F₇-nH H —C(CH₃)₂—OH H H 0521 —CO—C₃F₇-n H H —CH₂—OH H H 0522 —CO—C₃F₇-n H H—CO—CH₃ H H 0523 —CO—C₃F₇-n H H —C(═NOH)—CH₃ H H 0524 —CO—C₃F₇-n H H—CH(OH)—CH₃ H H 0525 —CO—C₃F₇-n H H (3) —CO—O—CH₂— (4) H 0526 —CO—C₃F₇-nH H —CH₂—O—CO—CH₃ H H 0527 —CO—C₃F₇-n H H —C(═NO—CH₃)—CH₃ H H 0528—CO—C₃F₇-n H H —CO—O—CH₃ H H 0529 —CO—C₃F₇-n H H —NH—CO—C₃H₅-cycl. H H0530 —CO—C₃F₇-n H H —CO—CH₃ Cl H 0531 —CO—C₃F₇-n H H —OH H H 0532—CO—C₃F₇-n H H —OH —OCH₃ H 0533 —CO—C₃F₇-n H H —OCH₃ H —OCH₃ 0534—CO—C₃F₇-n H H —SCH₃ H H 0535 —CO—C₃F₇-n H H —OCH₃ H H 0536 —CO—C₃F₇-n HH —OCH₃ —OCH₃ —OCH₃ 0537 —CO—C₃F₇-n H H —OH —OCH₃ —OCH₃ 0538 —CO—C₃F₇-nH H H —SCH₃ H 0539 —CO—C₃F₇-n H H H —OCH₃ H 0540 —CO—C₃F₇-n H H —OCH₃—OH H 0541 —CO—C₃F₇-n H —OCH₃ —CH₃ H H 0542 —CO—C₃F₇-n H H —CH₂—CH₃ H H0543 —CO—C₃F₇-n H —OCH₃ —CH(CH₃)₂ H H 0544 —CO—C₃F₇-n H H —C₃H₇-n H H0545 —CO—C₃F₇-n H H —OCH₂—CH₃ H H 0546 —CO—C₃F₇-n H H F H H 0547—CO—C₃F₇-u H H Cl H H 0548 —CO—C₃F₇-n H H Br H H 0549 —CO—C₃F₇-n H H ClCl H 0550 —CO—C₃F₇-n H H OH OH OH 0551 —CO—C₃F₇-n H Cl Cl H Cl 0552—CO—C₃F₇-n H H —CF₃ H H 0553 —CO—C₃F₇-n H H —C₂F₅ H H 0554 —CO—C₃F₇-n HH —C₄H₉-tert H H 0555 —CO—C₃F₇-n H H —OC₃H₇-i H H 0556 —CO—C₃F₇-n H H—SO—CH₃ H H 0557 —CO—C₃F₇-n H H —SO₂—CH₃ H H 0558 —CO—C₃F₇-n H H—NH—CH₂—CH₃ H H 0559 —CO—C₃F₇-n H H —O—CH₂—CH═CH₂ H H 0560 —CO—C₃F₇-n HH —O—CH₂—C═CH H H 0561 —CO—C₃F₇-n H H —NH—CH₂—CH₂—NH—CH₃ H H 0562—CO—C₃F₇-n H H —SO₂—C₂H₅ H H 0563 —CO—C₃F₇-n H H —SO₂—CH₃ Cl H 0564—CO—CH₂—O—CO—CH₃ H H —CH₂—O—CH₃ H H 0565 —CO—CH₂—O—CO—CH₃ H H —NH—CO—CH₃H H 0566 —CO—CH₂—O—CO—CH₃ H H —CH₂—NH—CO—CH₃ H H 0567 —CO—CH₂—O—CO—CH₃ HH —CH(CH₃)—NH—CO—CH₃ H H 0568 —CO—CH₂—O—CO—CH₃ H H —C(CH₃)₂—NH—CO—CH₃ HH 0569 —CO—CH₂—O—CO—CH₃ H H —CH(CH₃)—O—CH₃ H H 0570 —CO—CH₂—O—CO—CH₃ H H—C(CH₃)₂—O—CH₃ H H 0571 —CO—CH₂—O—CO—CH₃ H H —CH(CH₃)—O—CO—CH₃ H H 0572—CO—CH₂—O—CO—CH₃ H H —CH₂—O—CO—CH₃ H H 0573 —CO—CH₂—O—CO—CH₃ H H—C(CH₃)₂—O—CO—CH₃ H H 0574 —CO—CH₂—O—CO—CH₃ H H —CH₂—CH₂—O—H H H 0575—CO—CH₂—O—CO—CH₃ H H —CH₂—CH₂—O—CH₃ H H 0576 —CO—CH₂—O—CO—CH₃ H H

H H 0577 —CO—CH₂—O—CO—CH₃ H H

H H 0578 —CO—CH₂—O—CO—CH₃ H H

H H 0579 —CO—CH₂—O—CO—CH₃ H H

H H 0580 —CO—CH₂—O—CO—CH₃ H H

H H 0581 —CO—CH₂—O—CO—CH₃ H H

H H 0582 —CO—CH₂—O—CO—CH₃ H H

H H 0583 —CO—CH₂—O—CO—CH₃ H H

H H 0584 —CO—CH₂—O—CO—CH₃ H H

H H 0585 —CO—CH₂—O—CO—CH₃ H H

H H 0586 —CO—CH₂—O—CO—CH₃ H H

H H 0587 —CO—CH₂—O—CO—CH₃ H H

H H 0588 —CO—CH₂—O—CO—CH₃ H H H H H 0589 —CO—CH₂—O—CO—CH₃ H H CN H H0590 —CO—CH₂—O—CO—CH₃ H H —C(CH₃)₂—OH H H 0591 —CO—CH₂—O—CO—CH₃ H H—CH₂—OH H H 0592 —CO—CH₂—O—CO—CH₃ H H —CO—CH₃ H H 0593 —CO—CH₂—O—CO—CH₃H H —C(═NOH)—CH₃ H H 0594 —CO—CH₂—O—CO—CH₃ H H —CH(OH)—CH₃ H H 0595—CO—CH₂—O—CO—CH₃ H H (3) —CO—O—CH₂— (4) H 0596 —CO—CH₂—O—CO—CH₃ H H—CH₂—O—CO—CH₃ H H 0597 —CO—CH₂—O—CO—CH₃ H H —C(═NO—CH₃)—CH₃ H H 0598—CO—CH₂—O—CO—CH₃ H H —CO—O—CH₃ H H 0599 —CO—CH₂—O—CO—CH₃ H H—NH—CO—C₃H₅-cycl. H H 0600 —CO—CH₂—O—CO—CH₃ H H —CO—CH₃ Cl H 0601—CO—CH₂—O—CO—CH₃ H H —OH H H 0602 —CO—CH₂—O—CO—CH₃ H H —OH —OCH₃ H 0603—CO—CH₂—O—CO—CH₃ H H —OCH₃ H —OCH₃ 0604 —CO—CH₂—O—CO—CH₃ H H —SCH₃ H H0605 —CO—CH₂—O—CO—CH₃ H H —OCH₃ H H 0606 —CO—CH₂—O—CO—CH₃ H H —OCH₃—OCH₃ —OCH₃ 0607 —CO—CH₂—O—CO—CH₃ H H —OH —OCH₃ —OCH₃ 0608—CO—CH₂—O—CO—CH₃ H H H —SCH₃ H 0609 —CO—CH₂—O—CO—CH₃ H H H —OCH₃ H 0610—CO—CH₂—O—CO—CH₃ H H —OCH₃ —OH H 0611 —CO—CH₂—O—CO—CH₃ H —OCH₃ —CH₃ H H0612 —CO—CH₂—O—CO—CH₃ H H —CH₂—CH₃ H H 0613 —CO—CH₂—O—CO—CH₃ H —OCH₃—CH(CH₃)₂ H H 0614 —CO—CH₂—O—CO—CH₃ H H —C₃H₇-n H H 0615—CO—CH₂—O—CO—CH₃ H H —OCH₂—CH₃ H H 0616 —CO—CH₂—O—CO—CH₃ H H F H H 0617—CO—CH₂—O—CO—CH₃ H H Cl H H 0618 —CO—CH₂—O—CO—CH₃ H H Br H H 0619—CO—CH₂—O—CO—CH₃ H H Cl Cl H 0620 —CO—CH₂—O—CO—CH₃ H H OH OH OH 0621—CO—CH₂—O—CO—CH₃ H Cl Cl H Cl 0622 —CO—CH₂—O—CO—CH₃ H H —CF₃ H H 0623—CO—CH₂—O—CO—CH₃ H H —OCF₃ H H 0624 —CO—CH₂—O—CO—CH₃ H H —C₂F₅ H H 0625—CO—CH₂—O—CO—CH₃ H H —C₄H₉-tert H H 0626 —CO—CH₂—O—CO—CH₃ H H —OC₃H₇-i HH 0627 —CO—CH₂—O—CO—CH₃ H H —SO—CH₃ H H 0628 —CO—CH₂—O—CO—CH₃ H H—SO₂—CH₃ H H 0629 —CO—CH₂—O—CO—CH₃ H H —NH—CH₂—CH₃ H H 0630—CO—CH₂—O—CO—CH₃ H H —O—CH₂—CH═CH₂ H H 0631 —CO—CH₂—O—CO—CH₃ H H—O—CH₂—C═CH H H 0632 —CO—CH₂—O—CO—CH₃ H H —NH—CH₂—CH₂—NH—CH₃ H H 0633—CO—CH₂—O—CO—CH₃ H H —SO₂—C₂H₅ H H 0634 —CO—CH₂—O—CO—CH₃ H H —SO₂—CH₃ ClH 0635 —CO—C₂F₅ H H —CH₂—O—CH₃ H H 0636 —CO—C₂F₅ H H —NH—CO—CH₃ H H 0637—CO—C₂F₅ H H —CH₂—NH—CO—CH₃ H H 0638 —CO—C₂F₅ H H —CH(CH₃)—NH—CO—CH₃ H H0639 —CO—C₂F₅ H H —C(CH₃)₂—NH—CO—CH₃ H H 0640 —CO—C₂F₅ H H—CH(CH₃)—O—CH₃ H H 0641 —CO—C₂F₅ H H —C(CH₃)₂—O—CH₃ H H 0642 —CO—C₂F₅ HH —CH(CH₃)—O—CO—CH₃ H H 0643 —CO—C₂F₅ H H —CH₂—O—CO—CH₃ H H 0644—CO—C₂F₅ H H —C(CH₃)₂—O—CO—CH₃ H H 0645 —CO—C₂F₅ H H —CH₂—CH₂—O—H H H0646 —CO—C₂F₅ H H —CH₂—CH₂—O—CH₃ H H 0647 —CO—C₂F₅ H H

H H 0648 —CO—C₂F₅ H H

H H 0649 —CO—C₂F₅ H H

H H 0650 —CO—C₂F₅ H H

H H 0651 —CO—C₂F₅ H H

H H 0652 —CO—C₂F₅ H H

H H 0653 —CO—C₂F₅ H H

H H 0654 —CO—C₂F₅ H H

H H 0655 —CO—C₂F₅ H H

H H 0656 —CO—C₂F₅ H H

H H 0657 —CO—C₂F₅ H H

H H 0658 —CO—C₂F₅ H H H H H 0659 —CO—C₂F₅ H H CN H H 0660 —CO—C₂F₅ H H—C(CH₃)₂—OH H H 0661 —CO—C₂F₅ H H —CH₂—OH H H 0662 —CO—C₂F₅ H H —CO—CH₃H H 0663 —CO—C₂F₅ H H —C(═NOH)—CH₃ H H 0664 —CO—C₂F₅ H H —CH(OH)—CH₃ H H0665 —CO—C₂F₅ H H (3) —CO—O—CH₂— (4) H 0666 —CO—C₂F₅ H H —CH₂—O—CO—CH₃ HH 0667 —CO—C₂F₅ H H —C(═NO—CH₃)—CH₃ H H 0668 —CO—C₂F₅ H H —CO—O—CH₃ H H0669 —CO—C₂F₅ H H —NH—CO—C₃H₅-cycl. H H 0670 —CO—C₂F₅ H H —CO—CH₃ Cl H0671 —CO—C₂F₅ H H —OH H H 0672 —CO—C₂F₅ H H —OH —OCH₃ H 0673 —CO—C₂F₅ HH —OCH₃ H —OCH₃ 0674 —CO—C₂F₅ H H —SCH₃ H H 0675 —CO—C₂F₅ H H —OCH₃ H H0676 —CO—C₂F₅ H H —OCH₃ —OCH₃ —OCH₃ 0677 —CO—C₂F₅ H H —OH —OCH₃ —OCH₃0678 —CO—C₂F₅ H H H —SCH₃ H 0679 —CO—C₂F₅ H H H —OCH₃ H 0680 —CO—C₂F₅ HH —OCH₃ —OH H 0681 —CO—C₂F₅ H —OCH₃ —CH₃ H H 0682 —CO—C₂F₅ H H —CH₂—CH₃H H 0683 —CO—C₂F₅ H —OCH₃ —CH(CH₃)₂ H H 0684 —CO—C₂F₅ H H —C₃H₇-n H H0685 —CO—C₂F₅ H H —OCH₂—CH₃ H H 0686 —CO—C₂F₅ H H F H H 0687 —CO—C₂F₅ HH Cl H H 0688 —CO—C₂F₅ H H Br H H 0689 —CO—C₂F₅ H H Cl Cl H 0690—CO—C₂F₅ H H OH OH OH 0691 —CO—C₂F₅ H Cl Cl H Cl 0692 —CO—C₂F₅ H H —CF₃H H 0693 —CO—C₂F₅ H H —OCF₃ H H 0694 —CO—C₂F₅ H H —C₂F₅ H H 0695—CO—C₂F₅ H H —C₄H₉-tert H H 0696 —CO—C₂F₅ H H —OC₃H₇-i H H 0697 —CO—C₂F₅H H —SO—CH₃ H H 0698 —CO—C₂F₅ H H —SO₂—CH₃ H H 0699 —CO—C₂F₅ H H —NH—CH₂—CH₃ H H 0700 —CO—C₂F₅ H H —O—CH₂—CH═CH₂ H H 0701 —CO—C₂F₅ H H—O—CH₂—C═CH H H 0702 —CO—C₂F₅ H H —NH—CH₂—CH₂—NH—CH₃ H H 0703 —CO—C₂F₅ HH —SO₂—C₂H₅ H H 0704 —CO—C₂F₅ H H —SO₂—CH₃ Cl H 0705 —CO—CF₃ H H—CH₂—O—CH₃ H H 0706 —CO—CF₃ H H —NH—CO—CH₃ H H 0707 —CO—CF₃ H H—CH₂—NH—CO—CH₃ H H 0708 —CO—CF₃ H H —CH(CH₃)—NH—CO—CH₃ H H 0709 —CO—CF₃H H —C(CH₃)₂—NH—CO—CH₃ H H 0710 —CO—CF₃ H H —CH(CH₃)—O—CH₃ H H 0711—CO—CF₃ H H —C(CH₃)₂—O—CH₃ H H 0712 —CO—CF₃ H H —CH(CH₃)—O—CO—CH₃ H H0713 —CO—CF₃ H H —CH₂—O—CO—CH₃ H H 0714 —CO—CF₃ H H —C(CH₃)₂—O—CO—CH₃ HH 0715 —CO—CF₃ H H —CH₂—CH₂—O—H H H 0716 —CO—CF₃ H H —CH₂—CH₂—O—CH₃ H H0717 —CO—CF₃ H H

H H 0718 —CO—CF₃ H H

H H 0719 —CO—CF₃ H H

H H 0720 —CO—CF₃ H H

H H 0721 —CO—CF₃ H H

H H 0722 —CO—CF₃ H H

H H 0723 —CO—CF₃ H H

H H 0724 —CO—CF₃ H H

H H 0725 —CO—CF₃ H H

H H 0726 —CO—CF₃ H H

H H 0727 —CO—CF₃ H H

H H 0728 —CO—CF₃ H H

H H 0729 —CO—CF₃ H H H H H 0730 —CO—CF₃ H H CN H H 0731 —CO—CF₃ H H—C(CH₃)₂—OH H H 0732 —CO—CF₃ H H —CH₂—OH H H 0733 —CO—CF₃ H H —CO—CH₃ HH 0734 —CO—CF₃ H H —C(═NOH)—CH₃ H H 0735 —CO—CF₃ H H —CH(OH)—CH₃ H H0736 —CO—CF₃ H H (3) —CO—O—CH₂— (4) H 0737 —CO—CF₃ H H —CH₂—O—CO—CH₃ H H0738 —CO—CF₃ H H —C(═NO—CH₃)—CH₃ H H 0739 —CO—CF₃ H H —CO—O—CH₃ H H 0740—CO—CF₃ H H —NH—CO—C₃H₅-cycl. H H 0741 —CO—CF₃ H H —CO—CH₃ Cl H 0742—CO—CF₃ H H —OH H H 0743 —CO—CF₃ H H —OH —OCH₃ H 0744 —CO—CF₃ H H —OCH₃H —OCH₃ 0745 —CO—CF₃ H H —SCH₃ H H 0746 —CO—CF₃ H H —OCH₃ H H 0747—CO—CF₃ H H —OCH₃ —OCH₃ —OCH₃ 0748 —CO—CF₃ H H —OH —OCH₃ —OCH₃ 0749—CO—CF₃ H H H —SCH₃ H 0750 —CO—CF₃ H H H —OCH₃ H 0751 —CO—CF₃ H H —OCH₃—OH H 0752 —CO—CF₃ H —OCH₃ —CH₃ H H 0753 —CO—CF₃ H —OCH₃ —CH(CH₃)₂ H H0754 —CO—CF₃ H H —C₃H₇-n H H 0755 —CO—CF₃ H H —OCH₂—CH₃ H H 0756 —CO—CF₃H H F H H 0757 —CO—CF₃ H H Cl H H 0758 —CO—CF₃ H H Br H H 0759 —CO—CF₃ HH Cl Cl H 0760 —CO—CF₃ H H OH OH OH 0761 —CO—CF₃ H Cl Cl H Cl 0762—CO—CF₃ H H —CF₃ H H 0763 —CO—CF₃ H H —OCF₃ H H 0764 —CO—CF₃ H H —C₂F₅ HH 0765 —CO—CF₃ H H —C₄H₉-tert H H 0766 —CO—CF₃ H H —OC₃H₇-i H H 0767—CO—CF₃ H H —SO—CH₃ H H 0768 —CO—CF₃ H H —SO₂—CH₃ H H 0769 —CO—CF₃ H H—NH—CH₂—CH₃ H H 0770 —CO—CF₃ H H —O—CH₂—CH═CH₂ H H 0771 —CO—CF₃ H H—O—CH₂—C═CH H H 0772 —CO—CF₃ H H —NH—CH₂—CH₂—NH—CH₃ H H 0773 —CO—CF₃ H H—SO₂—C₂H₅ H H 0774 —CO—CF₃ H H —SO₂—CH₃ Cl H 0775 —(CH₂)₄— H —CH₂—O—CH₃H H 0776 —(CH₂)₄— H —NH—CO—CH₃ H H 0777 —(CH₂)₄— H —CH₂—NH—CO—CH₃ H H0778 —(CH₂)₄— H —CH(CH₃)—NH—CO—CH₃ H H 0779 —(CH₂)₄— H—C(CH₃)₂—NH—CO—CH₃ H H 0780 —(CH₂)₄— H —CH(CH₃)—O—CH₃ H H 0781 —(CH₂)₄—H —C(CH₃)₂—O—CH₃ H H 0782 —(CH₂)₄— H —CH(CH₃)—O—CO—CH₃ H H 0783 —(CH₂)₄—H —CH₂—O—CO—CH₃ H H 0784 —(CH₂)₄— H —C(CH₃)₂—O—CO—CH₃ H H 0785 —(CH₂)₄—H —CH₂—CH₂—O—H H H 0786 —(CH₂)₄— H —CH₂—CH₂—O—CH₃ H H 0787 —(CH₂)₄— H

H H 0788 —(CH₂)₄— H

H H 0789 —(CH₂)₄— H

H H 0790 —(CH₂)₄— H

H H 0791 —(CH₂)₄— H

H H 0792 —(CH₂)₄— H

H H 0793 —(CH₂)₄— H

H H 0794 —(CH₂)₄— H

H H 0795 —(CH₂)₄— H

H H 0796 —(CH₂)₄— H

H H 0797 —(CH₂)₄— H

H H 0798 —(CH₂)₄— H

H H 0799 —(CH₂)₄— H H H H 0800 —(CH₂)₄— H CN H H 0801 —(CH₂)₄— H—C(CH₃)₂—OH H H 0802 —(CH₂)₄— H —CH₂—OH H H 0803 —(CH₂)₄— H —CO—CH₃ H H0804 —(CH₂)₄— H —C(═NOH)—CH₃ H H 0805 —(CH₂)₄— H —CH(OH)—CH₃ H H 0806—(CH₂)₄— H (3) —CO—O—CH₂— (4) H 0807 —(CH₂)₄— H —CH₂—O—CO—CH₃ H H 0808—(CH₂)₄— H —C(═NO—CH₃)—CH₃ H H 0809 —(CH₂)₄— H —CO—O—CH₃ H H 0810—(CH₂)₄— H —NH—CO—C₃H₅-cycl. H H 0811 —(CH₂)₄— H —CO—CH₃ Cl H 0812—(CH₂)₄— H —OH H H 0813 —(CH₂)₄— H —OH —OCH₃ H 0814 —(CH₂)₄— H —OCH₃ H—OCH₃ 0815 —(CH₂)₄— H —SCH₃ H H 0816 —(CH₂)₄— H —OCH₃ H H 0817 —(CH₂)₄—H —OCH₃ —OCH₃ —OCH₃ 0818 —(CH₂)₄— H —OH —OCH₃ —OCH₃ 0819 —(CH₂)₄— H H—SCH₃ H 0820 —(CH₂)₄— H H —OCH₃ H 0821 —(CH₂)₄— H —OCH₃ —OH H 0822—(CH₂)₄— —OCH₃ —CH₃ H H 0823 —(CH₂)₄— H —CH₂—CH₃ H H 0824 —(CH₂)₄— —OCH₃—CH(CH₃)₂ H H 0825 —(CH₂)₄— H —C₃H₇-n H H 0826 —(CH₂)₄— H —OCH₂—CH₃ H H0827 —(CH₂)₄— H F H H 0828 —(CH₂)₄— H Cl H H 0829 —(CH₂)₄— H Br H H 0830—(CH₂)₄— H Cl Cl H 0831 —(CH₂)₄— H OH OH OH 0832 —(CH₂)₄— Cl Cl H Cl0833 —(CH₂)₄— H —CF₃ H H 0834 —(CH₂)₄— H —OCF₃ H H 0835 —(CH₂)₄— H —C₂F₅H H 0836 —(CH₂)₄— H —C₄H₉-tert H H 0837 —(CH₂)₄— H —OC₃H₇-i H H 0838—(CH₂)₄— H —SO—CH₃ H H 0839 —(CH₂)₄— H —SO₂—CH₃ H H 0840 —(CH₂)₄— H—NH—CH₂—CH₃ H H 0841 —(CH₂)₄— H —O—CH₂—CH═CH₂ H H 0842 —(CH₂)₄— H—O—CH₂—C═CH H H 0843 —(CH₂)₄— H —NH—CH₂—CH₂—NH—CH₃ H H 0844 —(CH₂)₄— H—SO₂—C₂H₅ H H 0845 —(CH₂)₄— H —SO₂—CH₃ Cl H 0846 —N═C(CH₃)—N(CH₃)₂ H—CH₂—O—CH₃ H H 0847 —N═C(CH₃)—N(CH₃)₂ H —NH—CO—CH₃ H H 0848—N═C(CH₃)—N(CH₃)₂ H —CH₂—NH—CO—CH₃ H H 0849 —N═C(CH₃)—N(CH₃)₂ H—CH(CH₃)—NH—CO—CH₃ H H 0850 —N═C(CH₃)—N(CH₃)₂ H —C(CH₃)₂—NH—CO—CH₃ H H0851 —N═C(CH₃)—N(CH₃)₂ H —CH(CH₃)—O—CH₃ H H 0852 —N═C(CH₃)—N(CH₃)₂ H—C(CH₃)₂—O—CH₃ H H 0853 —N═C(CH₃)—N(CH₃)₂ H —CH₂—O—CO—CH₃ H H 0854—N═C(CH₃)—N(CH₃)₂ H —C(CH₃)₂—O—CO—CH₃ H H 0855 —N═C(CH₃)—N(CH₃)₂ H—CH₂—CH₂—O—H H H 0856 —N═C(CH₃)—N(CH₃)₂ H —CH₂—CH₂—O—CH₃ H H 0857—N═C(CH₃)—N(CH₃)₂ H

H H 0858 —N═C(CH₃)—N(CH₃)₂ H

H H 0859 —N═C(CH₃)—N(CH₃)₂ H

H H 0860 —N═C(CH₃)—N(CH₃)₂ H

H H 0861 —N═C(CH₃)—N(CH₃)₂ H

H H 0862 —N═C(CH₃)—N(CH₃)₂ H

H H 0863 —N═C(CH₃)—N(CH₃)₂ H

H H 0864 —N═C(CH₃)—N(CH₃)₂ H

H H 0865 —N═C(CH₃)—N(CH₃)₂ H

H H 0866 —N═C(CH₃)—N(CH₃)₂ H

H H 0867 —N═C(CH₃)—N(CH₃)₂ H

H H 0868 —N═C(CH₃)—N(CH₃)₂ H

H H 0869 —N═C(CH₃)—N(CH₃)₂ H H H H 0870 —N═C(CH₃)—N(CH₃)₂ H CN H H 0871—N═C(CH₃)—N(CH₃)₂ H —C(CH₃)₂—OH H H 0872 —N═C(CH₃)—N(CH₃)₂ H —CH₂—OH H H0873 —N═C(CH₃)—N(CH₃)₂ H —CO—CH₃ H H 0874 —N═C(CH₃)—N(CH₃)₂ H—C(═NOH)—CH₃ H H 0875 —N═C(CH₃)—N(CH₃)₂ H —CH(OH)—CH₃ H H 0876—N═C(CH₃)—N(CH₃)₂ H (3) —CO—O—CH₂— (4) H 0877 —N═C(CH₃)—N(CH₃)₂ H—CH₂—O—CO—CH₃ H H 0878 —N═C(CH₃)—N(CH₃)₂ H —C(═NO—CH₃)—CH₃ H H 0879—N═C(CH₃)—N(CH₃)₂ H —CO—O—CH₃ H H 0880 —N═C(CH₃)—N(CH₃)₂ H—NH—CO—C₃H₅-cycl. H H 0881 —N═C(CH₃)—N(CH₃)₂ H —CO—CH₃ Cl H 0882—N═C(CH₃)—N(CH₃)₂ H —OH H H 0883 —N═C(CH₃)—N(CH₃)₂ H —OH —OCH₃ H 0884—N═C(CH₃)—N(CH₃)₂ H —OCH₃ H —OCH₃ 0885 —N═C(CH₃)—N(CH₃)₂ H —SCH₃ H H0886 —N═C(CH₃)—N(CH₃)₂ H —OCH₃ H H 0887 —N═C(CH₃)—N(CH₃)₂ H OCH₃ —OCH₃—OCH₃ 0888 —N═C(CH₃)—N(CH₃)₂ H —OH —OCH₃ —OCH₃ 0889 —N═C(CH₃)—N(CH₃)₂ HH —SCH₃ H 0890 —N═C(CH₃)—N(CH₃)₂ H H —SCH₃ H 0891 —N═C(CH₃)—N(CH₃)₂ H—OCH₃ —OH H 0892 —N═C(CH₃)—N(CH₃)₂ —OCH₃ —CH₃ H H 0893 —N═C(CH₃)—N(CH₃)₂H —CH₂—CH₃ H H 0894 —N═C(CH₃)—N(CH₃)₂ —OCH₃ —CH(CH₃)_(2 H) H 0895—N═C(CH₃)—N(CH₃)₂ H —C₃H₇-n H H 0896 —N═C(CH₃)—N(CH₃)₂ H —OCH₂—CH₃ H H0897 —N═C(CH₃)—N(CH₃)₂ H F H H 0898 —N═C(CH₃)—N(CH₃)₂ H Cl H H 0899—N═C(CH₃)—N(CH₃)₂ H Br H H 0900 —N═C(CH₃)—N(CH₃)₂ H Cl Cl H 0901—N═C(CH₃)—N(CH₃)₂ H OH OH OH 0902 —N═C(CH₃)—N(CH₃)₂ Cl Cl H Cl 0903—N═C(CH₃)—N(CH₃)₂ H —CF₃ H H 0904 —N═C(CH₃)—N(CH₃)₂ H —OCF₃ H H 0905—N═C(CH₃)—N(CH₃)₂ H —C₂F₅ H H 0906 —N═C(CH₃)—N(CH₃)₂ H —C₄H₉-tert H H0907 —N═C(CH₃)—N(CH₃)₂ H —OC₃H₇-i H H 0908 —N═C(CH₃)—N(CH₃)₂ H —SO—CH₃ HH 0909 —N═C(CH₃)—N(CH₃)₂ H —SO₂—CH₃ H H 0910 —N═C(CH₃)—N(CH₃)₂ H—NH—CH₂—CH₃ H H 0911 —N═C(CH₃)—N(CH₃)₂ H —O—CH₂—CH═CH₂ H H 0912—N═C(CH₃)—N(CH₃)₂ H —O—CH₂—C═CH H H 0913 —N═C(CH₃)—N(CH₃)₂ H—NH—CH₂—CH₂—NH—CH₃ H H 0914 —N═C(CH₃)—N(CH₃)₂ H —SO₂—C₂H₅ H H 0915—N═C(CH₃)—N(CH₃)₂ H —SO₂—CH₃ Cl H 0916 —N═CH—N(CH₃)₂ H —CH₂—O—CH₃ H H0917 —N═CH—N(CH₃)₂ H —NH—CO—CH₃ H H 0918 —N═CH—N(CH₃)₂ H —CH₂—NH—CO—CH₃H H 0919 —N═CH—N(CH₃)₂ H —CH(CH₃)—NH—CO—CH₃ H H 0920 —N═CH—N(CH₃)₂ H—C(CH₃)₂—NH—CO—CH₃ H H 0921 —N═CH—N(CH₃)₂ H —CH(CH₃)—O—CH₃ H H 0922—N═CH—N(CH₃)₂ H —C(CH₃)₂—O—CH₃ H H 0923 —N═CH—N(CH₃)₂ H—CH(CH₃)—O—CO—CH₃ H H 0924 —N═CH—N(CH₃)₂ H —CH₂—O—CO—CH₃ H H 0925—N═CH—N(CH₃)₂ H —C(CH₃)₂—O—CO—CH₃ H H 0926 —N═CH—N(CH₃)₂ H —CH₂—CH₂—O—HH H 0927 —N═CH—N(CH₃)₂ H —CH₂—CH₂—O—CH₃ H H 0928 —N═CH—N(CH₃)₂ H

H H 0929 —N═CH—N(CH₃)₂ H

H H 0930 —N═CH—N(CH₃)₂ H

H H 0931 —N═CH—N(CH₃)₂ H

H H 0932 —N═CH—N(CH₃)₂ H

H H 0933 —N═CH—N(CH₃)₂ H

H H 0934 —N═CH—N(CH₃)₂ H

H H 0935 —N═CH—N(CH₃)₂ H

H H 0936 —N═CH—N(CH₃)₂ H

H H 0937 —N═CH—N(CH₃)₂ H

H H 0938 —N═CH—N(CH₃)₂ H

H H 0939 —N═CH—N(CH₃)₂ H

H H 0940 —N═CH—N(CH₃)₂ H H H H 0941 —N═CH—N(CH₃)₂ H CN H H 0942—N═CH—N(CH₃)₂ H —C(CH₃)₂—OH H H 0943 —N═CH—N(CH₃)₂ H —CH₂—OH H H 0944—N═CH—N(CH₃)₂ H —CO—CH₃ H H 0945 —N═CH—N(CH₃)₂ H —C(═NOH)—CH₃ H H 0946—N═CH—N(CH₃)₂ H —CH(OH)—CH₃ H H 0947 —N═CH—N(CH₃)₂ H (3) —CO—O—CH₂— (4)H 0948 —N═CH—N(CH₃)₂ H —CH₂—O—CO—CH₃ H H 0949 —N═CH—N(CH₃)₂ H—C(═NO—CH₃)—CH₃ H H 0950 —N═CH—N(CH₃)₂ H —CO—O—CH₃ H H 0951—N═CH—N(CH₃)₂ H —NH—CO—C₃H₅-cycl. H H 0952 —N═CH—N(CH₃)₂ H —CO—CH₃ Cl H0953 —N═CH—N(CH₃)₂ H —OH —OCH₃ H 0954 —N═CH—N(CH₃)₂ H —OCH₃ H —OCH₃ 0955—N═CH—N(CH₃)₂ H —SCH₃ H H 0956 —N═CH—N(CH₃)₂ H —OCH₃ H H 0957—N═CH—N(CH₃)₂ H —OCH₃ —OCH₃ —OCH₃ 0958 —N═CH—N(CH₃)₂ H —OH —OCH₃ —OCH₃0959 —N═CH—N(CH₃)₂ H H —SCH₃ H 0960 —N═CH—N(CH₃)₂ H H —OCH₃ H 0961—N═CH—N(CH₃)₂ H —OCH₃ —OH H 0962 —N═CH—N(CH₃)₂ —OCH₃ —CH₃ H H 0963—N═CH—N(CH₃)₂ H —CH₂—CH₃ H H 0964 —N═CH—N(CH₃)₂ —OCH₃ —CH(CH₃)₂ H H 0965—N═CH—N(CH₃)₂ H —C₃H₇-n H H 0966 —N═CH—N(CH₃)₂ H —OCH₂—CH₃ H H 0967—N═CH—N(CH₃)₂ H F H H 0968 —N═CH—N(CH₃)₂ H Cl H H 0969 —N═CH—N(CH₃)₂ HBr H H 0970 —N═CH—N(CH₃)₂ H Cl Cl H 0971 —N═CH—N(CH₃)₂ H OH OH OH 0972—N═CH—N(CH₃)₂ Cl Cl H Cl 0973 —N═CH—N(CH₃)₂ H —CF₃ H H 0974—N═CH—N(CH₃)₂ H —OCF₃ H H 0975 —N═CH—N(CH₃)₂ H —C₂F₅ H H 0976—N═CH—N(CH₃)₂ H —C₄H₉-tert H H 0977 —N═CH—N(CH₃)₂ H —OC₃H₇-i H H 0978—N═CH—N(CH₃)₂ H —SO—CH₃ H H 0979 —N═CH—N(CH₃)₂ H —SO₂—CH₃ H H 0980—N═CH—N(CH₃)₂ H —NH—CH₂—CH₃ H H 0981 —N═CH—N(CH₃)₂ H —O—CH₂—CH═CH₂ H H0982 —N═CH—N(CH₃)₂ H —O—CH₂—C═CH H H 0983 —N═CH—N(CH₃)₂ H—NH—CH₂—CH₂—NH—CH₃ H H 0984 —N═CH—N(CH₃)₂ H —SO₂—C₂H₅ H H 0985—N═CH—N(CH₃)₂ H —SO₂—CH₃ Cl H 0986 H H —OH H —OCH₃ H 0987 H H —OCH₃ —CH₃H H 0988 H H H —SO—CH₃ H H 0989 —CO—C₃H₅-cycl H H —CH₂—O—CH₃ H H 0990—CO—C₃H₅-cycl H H —NH—CO—CH₃ H H 0991 —CO—C₃H₅-cycl H H —CH₂—NH—CO—CH₃ HH 0992 —CO—C₃H₅-cycl H H —CH(CH₃)—NH—CO—CH₃ H H 0993 —CO—C₃H₅-cycl H H—C(CH₃)₂—NH—CO—CH₃ H H 0994 —CO—C₃H₅-cycl H H —CH(CH₃)—O—CH₃ H H 0995—CO—C₃H₅-cycl H H —C(CH₃)₂—O—CH₃ H H 0996 —CO—C₃H₅-cycl H H—CH(CH₃)—O—CO—CH₃ H H 0997 —CO—C₃H₅-cycl H H —CH₂—O—CO—CH₃ H H 0998—CO—C₃H₅-cycl H H —C(CH₃)₂—O—CO—CH₃ H H 0999 —CO—C₃H₅-cycl H H—CH₂—CH₂—O—H H H 1000 —CO—C₃H₅-cycl H H —CH₂—CH₂—O—CH₃ H H 1001—CO—C₃H₅-cycl H H

H H 1002 —CO—C₃H₅-cycl H H

H H 1003 —CO—C₃H₅-cycl H H

H H 1004 —CO—C₃H₅-cycl H H

H H 1005 —CO—C₃H₅-cycl H H

H H 1006 —CO—C₃H₅-cycl H H

H H 1007 —CO—C₃H₅-cycl H H

H H 1008 —CO—C₃H₅-cycl H H

H H 1009 —CO—C₃H₅-cycl H H

H H 1010 —CO—C₃H₅-cycl H H

H H 1011 —CO—C₃H₅-cycl H H

H H 1012 —CO—C₃H₅-cycl H H

H H 1013 —CO—C₃H₅-cycl H H H H H 1014 —CO—C₃H₅-cycl H H CN H H 1015—CO—C₃H₅-cycl H H —C(CH₃)₂—OH H H 1016 —CO—C₃H₅-cycl H H —CH₂—OH H H1017 —CO—C₃H₅-cycl H H —CO—CH₃ H H 1018 —CO—C₃H₅-cycl H H —C(═NOH)—CH₃ HH 1019 —CO—C₃H₅-cycl H H —CH(OH)—CH₃ H H 1020 —CO—C₃H₅-cycl H H (3)—CO—O—CH₂— (4) H 1021 —CO—C₃H₅-cycl H H —CH₂—O—CO—CH₃ H H 1022—CO—C₃H₅-cycl H H —C(═NO—CH₃)—CH₃ H H 1023 —CO—C₃H₅-cycl H H —CO—O—CH₃ HH 1024 —CO—C₃H₅-cycl H H —NH—CO—C₃H₅-cycl. H H 1025 —CO—C₃H₅-cycl H H—CO—CH₃ Cl H 1026 —CO—C₃H₅-cycl H H —OH H H 1027 —CO—C₃H₅-cycl H H —OH—OCH₃ H 1028 —CO—C₃H₅-cycl H H —OCH₃ H —OCH₃ 1029 —CO—C₃H₅-cycl H H—SCH₃ H H 1030 —CO—C₃H₅-cycl H H —OCH₃ H H 1031 —CO—C₃H₅-cycl H H —OCH₃—OCH₃ —OCH₃ 1032 —CO—C₃H₅-cycl H H —OH —OCH₃ —OCH₃ 1033 —CO—C₃H₅-cycl HH H —SCH₃ H 1034 —CO—C₃H₅-cycl H H H —OCH₃ H 1035 —CO—C₃H₅-cycl H H—OCH₃ —OH H 1036 —CO—C₃H₅-cycl H —OCH₃ —CH₃ H H 1037 —CO—C₃H₅-cycl H H—CH₂—CH₃ H H 1038 —CO—C₃H₅-cycl H —OCH₃ —CH(CH₃)₂ H H 1039 —CO—C₃H₅-cyclH H —C₃H₇-n H H 1040 —CO—C₃H₅-cycl H H —OCH₂—CH₃ H H 1041 —CO—C₃H₅-cyclH H F H H 1042 —CO—C₃H₅-cycl H H Cl H H 1043 —CO—C₃H₅-cycl H H Br H H1044 —CO—C₃H₅-cycl H H Cl Cl H 1045 —CO—C₃H₅-cycl H H OH OH OH 1046—CO—C₃H₅-cycl H Cl Cl H Cl 1047 —CO—C₃H₅-cycl H H —CF₃ H H 1048—CO—C₃H₅-cycl H H —OCF₃ H H 1049 —CO—C₃H₅-cycl H H —C₂F₅ H H 1050—CO—C₃H₅-cycl H H —C₄H₉-tert H H 1051 —CO—C₃H₅-cycl H H —OC₃H₇-i H H1052 —CO—C₃H₅-cycl H H —SO—CH₃ H H 1053 —CO—C₃H₅-cycl H H —NH—CH₂—CH₃ HH 1054 —CO—C₃H₅-cycl H H —O—CH₂—CH═CH₂ H H 1055 —CO—C₃H₅-cycl H H—O—CH₂—C═CH H H 1056 —CO—C₃H₅-cycl H H —NH—CH₂—CH₂—NH—CH₃ H H 1057—CO—C₃H₅-cycl H H —SO₂—C₂H₅ H H 1058 —CO—C₃H₅-cycl H H —SO₂—CH₃ Cl H1059 —CO—C(CH₃)₂—CH₂—Cl H H —CH₂—O—CH₃ H H 1060 —CO—C(CH₃)₂—CH₂—Cl H H—NH—CO—CH₃ H H 1061 —CO—C(CH₃)₂—CH₂—Cl H H —CH₂—NH—CO—CH₃ H H 1062—CO—C(CH₃)₂—CH₂—Cl H H —CH(CH₃)—NH—CO—CH₃ H H 1063 —CO—C(CH₃)₂—CH₂—Cl HH —C(CH₃)₂—NH—CO—CH₃ H H 1064 —CO—C(CH₃)₂—CH₂—Cl H H —CH(CH₃)—O—CH₃ H H1065 —CO—C(CH₃)₂—CH₂—Cl H H —C(CH₃)₂—O—CH₃ H H 1066 —CO—C(CH₃)₂—CH₂—Cl HH —CH(CH₃)—O—CO—CH₃ H H 1067 —CO—C(CH₃)₂—CH₂—Cl H H —CH₂—O—CO—CH₃ H H1068 —CO—C(CH₃)₂—CH₂—Cl H H —C(CH₃)₂—O—CO—CH₃ H H 1069—CO—C(CH₃)₂—CH₂—Cl H H —CH₂—CH₂—O—H H H 1070 —CO—C(CH₃)₂—CH₂—Cl H H—CH₂—CH₂—O—CH₃ H H 1071 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1072 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1073 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1074 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1075 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1076 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1077 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1078 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1079 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1080 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1081 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1082 —CO—C(CH₃)₂—CH₂—Cl H H

H H 1083 —CO—C(CH₃)₂—CH₂—Cl H H H H H 1084 —CO—C(CH₃)₂—CH₂—Cl H H CN H H1085 —CO—C(CH₃)₂—CH₂—Cl H H —C(CH₃)₂—OH H H 1086 —CO—C(CH₃)₂—CH₂—Cl H H—CH₂—OH H H 1087 —CO—C(CH₃)₂—CH₂—Cl H H —CO—CH₃ H H 1088—CO—C(CH₃)₂—CH₂—Cl H H —C(═NOH)—CH₃ H H 1089 —CO—C(CH₃)₂—CH₂—Cl H H—CH(OH)—CH₃ H H 1090 —CO—C(CH₃)₂—CH₂—Cl H H (3) —CO—O—CH₂— (4) H 1091—CO—C(CH₃)₂—CH₂—Cl H H —CH₂—O—CO—CH₃ H H 1092 —CO—C(CH₃)₂—CH₂—Cl H H—C(═NO—CH₃)—CH₃ H H 1093 —CO—C(CH₃)₂—CH₂—Cl H H —CO—O—CH₃ H H 1094—CO—C(CH₃)₂—CH₂—Cl H H —NH—CO—C₃H₅-cycl. H H 1095 —CO—C(CH₃)₂—CH₂—Cl H H—CO—CH₃ Cl H 1096 —CO—C(CH₃)₂—CH₂—Cl H H —OH H H 1097 —CO—C(CH₃)₂—CH₂—ClH H —OH —OCH₃ H 1098 —CO—C(CH₃)₂—CH₂—Cl H H —OCH₃ H —OCH₃ 1099—CO—C(CH₃)₂—CH₂—Cl H H —SCH₃ H H 1100 —CO—C(CH₃)₂—CH₂—Cl H H —OCH₃ H H1101 —CO—C(CH₃)₂—CH₂—Cl H H —OCH₃ —OCH₃ —OCH₃ 1102 —CO—C(CH₃)₂—CH₂—Cl HH —OH —OCH₃ —OCH₃ 1103 —CO—C(CH₃)₂—CH₂—Cl H H H —SCH₃ H 1104—CO—C(CH₃)₂—CH₂—Cl H H H —OCH₃ H 1105 —CO—C(CH₃)₂—CH₂—Cl H H —OCH₃ —OH H1106 —CO—C(CH₃)₂—CH₂—Cl H —OCH₃ —CH₃ H H 1107 —CO—C(CH₃)₂—CH₂—Cl H H—CH₂—CH₃ H H 1108 —CO—C(CH₃)₂—CH₂—Cl H —OCH₃ —CH(CH₃)₂ H H 1109—CO—C(CH₃)₂—CH₂—Cl H H —C₃H₇-n H H 1110 —CO—C(CH₃)₂—CH₂—Cl H H —OCH₂—CH₃H H 1111 —CO—C(CH₃)₂—CH₂—Cl H H F H H 1112 —CO—C(CH₃)₂—CH₂—Cl H H Cl H H1113 —CO—C(CH₃)₂—CH₂—Cl H H Br H H 1114 —CO—C(CH₃)₂—CH₂—Cl H H Cl Cl H1115 —CO—C(CH₃)₂—CH₂—Cl H H OH OH OH 1116 —CO—C(CH₃)₂—CH₂—Cl H Cl Cl HCl 1117 —CO—C(CH₃)₂—CH₂—Cl H H —CF₃ H H 1118 —CO—C(CH₃)₂—CH₂—Cl H H—OCF₃ H H 1119 —CO—C(CH₃)₂—CH₂—Cl H H —C₂F₅ H H 1120 —CO—C(CH₃)₂—CH₂—ClH H —C₄H₉-tert H H 1121 —CO—C(CH₃)₂—CH₂—Cl H H —OC₃H₇-i H H 1122—CO—C(CH₃)₂—CH₂—Cl H H —SO—CH₃ H H 1123 —CO—C(CH₃)₂—CH₂—Cl H H —SO₂—CH₃H H 1124 —CO—C(CH₃)₂—CH₂—Cl H H —NH—CH₂—CH₃ H H 1125 —CO—C(CH₃)₂—CH₂—ClH H —O—CH₂—CH═CH₂ H H 1126 —CO—C(CH₃)₂—CH₂—Cl H H —O—CH₂—C═CH H H 1127—CO—C(CH₃)₂—CH₂—Cl H H —NH—CH₂—CH₂—NH—CH₃ H H 1128 —CO—C(CH₃)₂—CH₂—Cl HH —SO₂—C₂H₅ H H 1129 —CO—C(CH₃)₂—CH₂—Cl H H —SO₂—CH₃ Cl H 1130 H H H F HH 1131 CH₃ H H —OCF₃ H H 1132 CH₃ H H —CH₂—CH₂—O—CH₃ H H 1133 CH₃ CH₃ H—SCH₃ H H 1134 —CO—CH₃ H H —SO₂—CH₃ Cl H 1135 —CO—CH(CH₃)—C₂H₅ H H—C(═NOH)—CH₃ H H 1136 —CO—C₃F₇-n H H —OCF₃ H H 1137 —CO—C₂F₅ H H

H H 1138 —CO—CF₃ H H —CH₂—CH₃ H H 1139 —CO—C₃H₅-cycl H H —SO₂—CH₃ H H1140 —N═C(CH₃)—N(CH₃)₂ H —CH(CH₃)—O—CO—CH₃ H H 1141 —N═CH—N(CH₃)₂ H —OHH H 1143 —CO—C(CH₃)₂—CH₂—Cl H H —CH₂—CN H H 1144 —CO—C(CH₃)₂—CH₂—Cl H H—CH—(CH₃)—CN H H 1145 —CO—C(CH₃)₂—CH₂—Cl H H —C(CH₃)₂—CN H H 1146—CO—C(CH₃)₂—CH₂—Cl H H —CH—(C₂H₅)—CN H H 1147 —CO—C(CH₃)₂—CH₂—Cl H H—C(C₂H₅)₂—CN H H 1148 —CO—C(CH₃)₂—CH₂—Cl H H —CH₂—CH₂—CN H H 1149—CO—C(CH₃)₂—CH₂—Cl H H —CH(CH₃)—CH₂—CN H H 1150 —CO—C(CH₃)₂—CH₂—Cl H H—CH₂—CO₂—CH₃ H H 1151 —CO—C(CH₃)₂—CH₂—Cl H H —CH(CH₃)—CO₂—CH₃ H H 1152C₂H₅ H H —CH₂—CN H H 1153 C₂H₅ H H —CH—(CH₃)—CN H H 1154 C₂H₅ H H—C(CH₃)₂—CN H H 1155 C₂H₅ H H —CH—(C₂H₅)—CN H H 1156 C₂H₅ H H—C(C₂H₅)₂—CN H H 1157 C₂H₅ H H —CH₂—CH₂—CN H H 1158 C₂H₅ H H—CH(CH₃)—CH₂—CN H H 1159 C₂H₅ H H —CH₂—CO₂—CH₃ H H 1160 C₂H₅ H H—CH(CH₃)—CO₂—CH₃ H H 1161 CH₃ H H —CH₂—CN H H 1162 CH₃ H H —CH—(CH₃)—CNH H 1163 CH₃ H H —C(CH₃)₂—CN H H 1164 CH₃ H H —CH—(C₂H₅)—CN H H 1165 CH₃H H —C(C₂H₅)₂—CN H H 1166 CH₃ H H —CH₂—CH₂—CN H H 1167 CH₃ H H—CH(CH₃)—CH₂—CN H H 1168 CH₃ H H —CH₂—CO₂—CH₃ H H 1169 CH₃ H H—CH(CH₃)—CO₂—CH₃ H H 1170 CH₃ CH₃ H —CH₂—CN H H 1171 CH₃ CH₃ H—CH—(CH₃)—CN H H 1172 CH₃ CH₃ H —C(CH₃)₂—CN H H 1173 CH₃ CH₃ H—CH—(C₂H₅)—CN H H 1174 CH₃ CH₃ H —C(C₂H₅)₂—CN H H 1175 CH₃ CH₃ H—CH₂—CH₂—CN H H 1176 CH₃ CH₃ H —CH(CH₃)—CH₂—CN H H 1177 CH₃ CH₃ H—CH₂—CO₂—CH₃ H H 1178 CH₃ CH₃ H —CH(CH₃)—CO₂—CH₃ H H 1179 —CO—CH₃ H H—CH₂—CN H H 1180 —CO—CH₃ H H —CH—(CH₃)—CN H H 1181 —CO—CH₃ H H—C(CH₃)₂—CN H H 1182 —CO—CH₃ H H —CH—(C₂H₅)—CN H H 1183 —CO—CH₃ H H—C(C₂H₅)₂—CN H H 1184 —CO—CH₃ H H —CH₂—CH₂—CN H H 1185 —CO—CH₃ H H—CH(CH₃)—CH₂—CN H H 1186 —CO—CH₃ H H —CH₂—CO₂—CH₃ H H 1187 —CO—CH₃ H H—CH(CH₃)—CO₂—CH₃ H H 1188 —CO—C₂H₅ H H —CH₂—CN H H 1189 —CO—C₂H₅ H H—CH—(CH₃)—CN H H 1190 —CO—C₂H₅ H H —C(CH₃)₂—CN H H 1191 —CO—C₂H₅ H H—CH—(C₂H₅)—CN H H 1192 —CO—C₂H₅ H H —C(C₂H₅)₂—CN H H 1193 —CO—C₂H₅ H H—CH₂—CH₂—CN H H 1194 —CO—C₂H₅ H H —CH(CH₃)—CH₂—CN H H 1195 —CO—C₂H₅ H H—CH₂—CO₂—CH₃ H H 1196 —CO—C₂H₅ H H —CH(CH₃)—CO₂—CH₃ H H 1197—CO—CH(CH₃)—C₂H₅ H H —CH₂—CN H H 1198 —CO—CH(CH₃)—C₂H₅ H H —CH—(CH₃)—CNH H 1199 —CO—CH(CH₃)—C₂H₅ H H —C(CH₃)₂—CN H H 1200 —CO—CH(CH₃)—C₂H₅ H H—CH—(C₂H₅)—CN H H 1201 —CO—CH(CH₃)—C₂H₅ H H —C(C2IT5)₂—CN H H 1202—CO—CH(CH₃)—C₂H₅ H H —CH₂—CH₂—CN H H 1203 —CO—CH(CH₃)—C₂H₅ H H—CH(CH₃)—CH₂—CN H H 1204 —CO—CH(CH₃)—C₂H₅ H H —CH₂—CO₂—CH₃ H H 1205—CO—CH(CH₃)—C₂H₅ H H —CH(CH₃)—CO₂—CH₃ H H 1206 —CO—C₃F₇-n H H —CH₂—CN HH 1207 —CO—C₃F₇-n H H —CH—(CH₃)—CN H H 1208 —CO—C₃F₇-n H H —C(CH₃)₂—CN HH 1209 —CO—C₃F₇-n H H —CH—(C₂H₅)—CN H H 1210 —CO—C₃F₇-n H H —C(C₂H₅)₂—CNH H 1211 —CO—C₃F₇-n H H —CH₂—CH₂—CN H H 1212 —CO—C₃F₇-n H H—CH(CH₃)—CH₂—CN H H 1213 —CO—C₃F₇-n H H —CH₂—CO₂—CH₃ H H 1214 —CO—C₃F₇-nH H —CH(CH₃)—CO₂—CH₃ H H 1215 —CO—CH₂—O—CO—CH₃ H H —CH₂—CN H H 1216—CO—CH₂—O—CO—CH₃ H H —CH—(CH₃)—CN H H 1217 —CO—CH₂—O—CO—CH₃ H H—C(CH₃)₂—CN H H 1218 —CO—CH₂—O—CO—CH₃ H H —CH—(C₂H₅)—CN H H 1219—CO—CH₂—O—CO—CH₃ H H —C(C₂H₅)₂—CN H H 1220 —CO—CH₂—O—CO—CH₃ H H—CH₂—CH₂—CN H H 1221 —CO—CH₂—O—CO—CH₃ H H —CH(CH₃)—CH₂—CN H H 1222—CO—CH₂—O—CO—CH₃ H H —CH₂—CO₂—CH₃ H H 1223 —CO—CH₂—O—CO—CH₃ H H—CH(CH₃)—CO₂—CH₃ H H 1224 —CO—C₂F₅ H H —CH₂—CN H H 1225 —CO—C₂F₅ H H—CH—(CH₃)—CN H H 1226 —CO—C₂F₅ H H —C(CH₃)₂—CN H H 1227 —CO—C₂F₅ H H—CH—(C₂H₅)—CN H H 1228 —CO—C₂F₅ H H —C(C₂H₅)₂—CN H H 1229 —CO—C₂F₅ H H—CH₂—CH₂—CN H H 1230 —CO—C₂F₅ H H —CH(CH₃)—CH₂—CN H H 1231 —CO—C₂F₅ H H—CH₂—CO₂—CH₃ H H 1232 —CO—C₂F₅ H H —CH(CH₃)—CO₂—CH₃ H H 1233 —CO—CF₃ H H—CH₂—CN H H 1234 —CO—CF₃ H H —CH—(CH₃)—CN H H 1235 —CO—CF₃ H H—C(CH₃)₂—CN H H 1236 —CO—CF₃ H H —CH—(C₂H₅)—CN H H 1237 —CO—CF₃ H H—C(C₂H₅)₂—CN H H 1238 —CO—CF₃ H H —CH₂—CH₂—CN H H 1239 —CO—CF₃ H H—CH(CH₃)—CH₂—CN H H 1240 —CO—CF₃ H H —CH₂—CO₂—CH₃ H H 1241 —CO—CF₃ H H—CH(CH₃)—CO₂—CH₃ H H 1243 —(CH₂)₄— H —CH₂—CN H H 1244 —(CH₂)₄— H—CH—(CH₃)—CN H H 1245 —(CH₂)₄— H —C(CH₃)₂—CN H H 1246 —(CH₂)₄— H—CH—(C₂H₅)—CN H H 1247 —(CH₂)₄— H —C(C₂H₅)₂—CN H H 1248 —(CH₂)₄— H—CH₂—CH₂—CN H H 1249 —(CH₂)₄— H —CH(CH₃)—CH₂—CN H H 1250 —(CH₂)₄— H—CH₂—CO₂—CH₃ H H 1251 —(CH₂)₄— H —CH(CH₃)—CO₂—CH₃ H H 1252—N═C(CH₃)—N(CH₃)₂ H —CH₂—CN H H 1253 —N═C(CH₃)—N(CH₃)₂ H —CH—(CH₃)—CN HH 1254 —N═C(CH₃)—N(CH₃)₂ H —C(CH₃)₂—CN H H 1255 —N═C(CH₃)—N(CH₃)₂ H—CH—(C₂H₅)—CN H H 1256 —N═C(CH₃)—N(CH₃)₂ H —C(C₂H₅)₂—CN H H 1257—N═C(CH₃)—N(CH₃)₂ H —CH₂—CH₂—CN H H 1258 —N═C(CH₃)—N(CH₃)₂ H—CH(CH₃)—CH₂—CN H H 1259 —N═C(CH₃)—N(CH₃)₂ H —CH₂—CO₂—CH₃ H H 1260—N═C(CH₃)—N(CH₃)₂ H —CH(CH₃)—CO₂—CH₃ H H 1261 —N═CH—N(CH₃)₂ H —CH₂—CN HH 1262 —N═CH—N(CH₃)₂ H —CH—(CH₃)—CN H H 1263 —N═CH—N(CH₃)₂ H —C(CH₃)₂—CNH H 1264 —N═CH—N(CH₃)₂ H —CH—(C₂H₅)—CN H H 1265 —N═CH—N(CH₃)₂ H—C(C₂H₅)₂—CN H H 1266 —N═CH—N(CH₃)₂ H —CH₂—CH₂—CN H H 1267 —N═CH—N(CH₃)₂H —CH(CH₃)—CH₂—CN H H 1268 —N═CH—N(CH₃)₂ H —CH₂—CO₂—CH₃ H H 1269—N═CH—N(CH₃)₂ H —CH(CH₃)—CO₂—CH₃ H H 1270 —CO—C₃H₅-cycl H H —CH₂—CN H H1271 —CO—C₃H₅-cycl H H —CH—(CH₃)—CN H H 1272 —CO—C₃H₅-cycl H H—C(CH₃)₂—CN H H 1273 —CO—C₃H₅-cycl H H —CH—(C₂H₅)—CN H H 1274—CO—C₃H₅-cycl H H —C(C₂H₅)₂—CN H H 1275 —CO—C₃H₅-cycl H H —CH₂—CH₂—CN HH 1276 —CO—C₃H₅-cycl H H —CH(CH₃)—CH₂—CN H H 1277 —CO—C₃H₅-cycl H H—CH₂—CO₂—CH₃ H H 1278 —CO—C₃H₅-cycl H H —CH(CH₃)—CO₂—CH₃ H H 1279—CH₂—CH₂—O—CH₃ H H —CH₂—O—CH₃ H H 1280 —CH₂—CH₂—O—CH₃ H H —NH—CO—CH₃ H H1281 —CH₂—CH₂—O—CH₃ H H —CH₂—NH—CO—CH₃ H H 1282 —CH₂—CH₂—O—CH₃ H H—CH(CH₃)—NH—CO—CH₃ H H 1283 —CH₂—CH₂—O—CH₃ H H —C(CH₃)₂—NH—CO—CH₃ H H1284 —CH₂—CH₂—O—CH₃ H H —CH(CH₃)—O—CH₃ H H 1285 —CH₂—CH₂—O—CH₃ H H—C(CH₃)₂—O—CH₃ H H 1286 —CH₂—CH₂—O—CH₃ H H —CH(CH₃)—O—CO—CH₃ H H 1287—CH₂—CH₂—O—CH₃ H H —CH₂—O—CO—CH₃ H H 1288 —CH₂—CH₂—O—CH₃ H H—C(CH₃)₂—O—CO—CH₃ H H 1289 —CH₂—CH₂—O—CH₃ H H —CH₂—CH₂—O—H H H 1290—CH₂—CH₂—O—CH₃ H H —CH₂—CH₂—O—CH₃ H H 1291 —CH₂—CH₂—O—CH₃ H H

H H 1292 —CH₂—CH₂—O—CH₃ H H

H H 1293 —CH₂—CH₂—O—CH₃ H H

H H 1294 —CH₂—CH₂—O—CH₃ H H

H H 1295 —CH₂—CH₂—O—CH₃ H H

H H 1296 —CH₂—CH₂—O—CH₃ H H

H H 1297 —CH₂—CH₂—O—CH₃ H H

H H 1298 —CH₂—CH₂—O—CH₃ H H

H H 1299 —CH₂—CH₂—O—CH₃ H H

H H 1300 —CH₂—CH₂—O—CH₃ H H

H H 1301 —CH₂—CH₂—O—CH₃ H H

H H 1302 —CH₂—CH₂—O—CH₃ H H

H H 1303 —CH₂—CH₂—O—CH₃ H H H H H 1304 —CH₂—CH₂—O—CH₃ H H CN H H 1305—CH₂—CH₂—O—CH₃ H H —C(CH₃)₂—OH H H 1306 —CH₂—CH₂—O—CH₃ H H —CH₂—OH H H1307 —CH₂—CH₂—O—CH₃ H H —CO—CH₃ H H 1308 —CH₂—CH₂—O—CH₃ H H —C(═NOH)—CH₃H H 1309 —CH₂—CH₂—O—CH₃ H H —CH(OH)—CH₃ H H 1310 —CH₂—CH₂—O—CH₃ H H (3)—CO—O—CH₂— (4) H 1311 —CH₂—CH₂—O—CH₃ H H —CH₂—O—CO—CH₃ H H 1312—CH₂—CH₂—O—CH₃ H H —C(═NO—CH₃)—CH₃ H H 1313 —CH₂—CH₂—O—CH₃ H H —CO—O—CH₃H H 1314 —CH₂—CH₂—O—CH₃ H H —NH—CO—C₃H₅-cycl. H H 1315 —CH₂—CH₂—O—CH₃ HH —CO—CH₃ Cl H 1316 —CH₂—CH₂—O—CH₃ H H —OH H H 1317 —CH₂—CH₂—O—CH₃ H H—OH —OCH₃ H 1318 —CH₂—CH₂—O—CH₃ H H —OCH₃ H —OCH₃ 1319 —CH₂—CH₂—O—CH₃ HH —SCH₃ H H 1320 —CH₂—CH₂—O—CH₃ H H —OCH₃ H H 1321 —CH₂—CH₂—O—CH₃ H H—OCH₃ —OCH₃ —OCH₃ 1322 —CH₂—CH₂—O—CH₃ H H —OH —OCH₃ —OCH₃ 1323—CH₂—CH₂—O—CH₃ H H H —SCH₃ H 1324 —CH₂—CH₂—O—CH₃ H H H —OCH₃ H 1325—CH₂—CH₂—O—CH₃ H H —OCH₃ —OH H 1326 —CH₂—CH₂—O—CH₃ H —OCH₃ —CH₃ H H 1327—CH₂—CH₂—O—CH₃ H H H H 1328 —CH₂—CH₂—O—CH₃ H —OCH₃ —CH(CH₃)₂ H H 1329—CH₂—CH₂—O—CH₃ H H —C₃H₇-n H H 1330 —CH₂—CH₂—O—CH₃ H H —OCH₂—CH₃ H H1331 —CH₂—CH₂—O—CH₃ H H F H H 1332 —CH₂—CH₂—O—CH₃ H H Cl H H 1333—CH₂—CH₂—O—CH₃ H H Br H H 1334 —CH₂—CH₂—O—CH₃ H H Cl Cl H 1335—CH₂—CH₂—O—CH₃ H H OH OH OH 1336 —CH₂—CH₂—O—CH₃ H Cl Cl H Cl 1337—CH₂—CH₂—O—CH₃ H H —CF₃ H H 1338 —CH₂—CH₂—O—CH₃ H H —OCF₃ H H 1339—CH₂—CH₂—O—CH₃ H H —C₂F₅ H H 1340 —CH₂—CH₂—O—CH₃ H H —C₄H₉-tert H H 1341—CH₂—CH₂—O—CH₃ H H —OC₃H₇-i H H 1343 —CH₂—CH₂—O—CH₃ H H —SO—CH₃ H H 1344—CH₂—CH₂—O—CH₃ H H —SO₂—CH₃ H H 1345 —CH₂—CH₂—O—CH₃ H H —NH—CH₂—CH₃ H H1346 —CH₂—CH₂—O—CH₃ H H —O—CH₂—CH═CH₂ H H 1347 —CH₂—CH₂—O—CH₃ H H—O—CH₂—C═CH H H 1348 —CH₂—CH₂—O—CH₃ H H —NH—CH₂—CH₂—NH—CH₃ H H 1349—CH₂—CH₂—O—CH₃ H H —SO₂—C₂H₅ H H 1350 —CH₂—CH₂—O—CH₃ H H —SO₂—CH₃ Cl H1351 —CH₂—CH₂—O—CH₃ H H —CH₂—CN H H 1352 —CH₂—CH₂—O—CH₃ H H —CH—(CH₃)—CNH H 1353 —CH₂—CH₂—O—CH₃ H H —C(CH₃)₂—CN H H 1354 —CH₂—CH₂—O—CH₃ H H—CH—(C₂H₅)—CN H H 1355 —CH₂—CH₂—O—CH₃ H H —C(C₂H₅)₂—CN H H 1356—CH₂—CH₂—O—CH₃ H H —CH₂—CH₂—CN H H 1357 —CH₂—CH₂—O—CH₃ H H—CH(CH₃)—CH₂—CN H H 1358 —CH₂—CH₂—O—CH₃ H H —CH₂—CO₂—CH₃ H H 1359—CH₂—CH₂—O—CH₃ H H —CH(CH₃)—CO₂—CH₃ H H 1360 —CH(CH₃)—CH₂—O—CH₃ H H—CH₂—O—CH₃ H H 1361 —CH(CH₃)—CH₂—O—CH₃ H H —NH—CO—CH₃ H H 1362—CH(CH₃)—CH₂—O—CH₃ H H —CH₂—NH—CO—CH₃ H H 1363 —CH(CH₃)—CH₂—O—CH₃ H H—CH(CH₃)—NH—CO—CH₃ H H 1364 —CH(CH₃)—CH₂—O—CH₃ H H —C(CH₃)₂—NH—CO—CH₃ HH 1365 —CH(CH₃)—CH₂—O—CH₃ H H —CH(CH₃)—O—CH₃ H H 1366 —CH(CH₃)—CH₂—O—CH₃H H —C(CH₃)₂—O—CH₃ H H 1367 —CH(CH₃)—CH₂—O—CH₃ H H —CH(CH₃)—O—CO—CH₃ H H1368 —CH(CH₃)—CH₂—O—CH₃ H H —CH₂—O—CO—CH₃ H H 1369 —CH(CH₃)—CH₂—O—CH₃ HH —C(CH₃)₂—O—CO—CH₃ H H 1370 —CH(CH₃)—CH₂—O—CH₃ H H —CH₂—CH₂—O—H H H1371 —CH(CH₃)—CH₂—O—CH₃ H H —CH₂—CH₂—O—CH₃ H H 1372 —CH(CH₃)—CH₂—O—CH₃ HH

H H 1373 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1374 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1375 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1376 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1377 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1378 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1379 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1380 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1381 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1382 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1383 —CH(CH₃)—CH₂—O—CH₃ H H

H H 1384 —CH(CH₃)—CH₂—O—CH₃ H H H H H 1385 —CH(CH₃)—CH₂—O—CH₃ H H CN H H1386 —CH(CH₃)—CH₂—O—CH₃ H H —C(CH₃)₂—OH H H 1387 —CH(CH₃)—CH₂—O—CH₃ H H—CH₂—OH H H 1388 —CH(CH₃)—CH₂—O—CH₃ H H —CO—CH₃ H H 1389—CH(CH₃)—CH₂—O—CH₃ H H —C(═NOH)—CH₃ H H 1390 —CH(CH₃)—CH₂—O—CH₃ H H—CH(OH)—CH₃ H H 1391 —CH(CH₃)—CH₂—O—CH₃ H H (3) —CO—O—CH₂— (4) H 1392—CH(CH₃)—CH₂—O—CH₃ H H —CH₂—O—CO—CH₃ H H 1393 —CH(CH₃)—CH₂—O—CH₃ H H—C(═NO—CH₃)—CH₃ H H 1394 —CH(CH₃)—CH₂—O—CH₃ H H —CO—O—CH₃ H H 1395—CH(CH₃)—CH₂—O—CH₃ H H —NH—CO—C₃H₅-cycl. H H 1396 —CH(CH₃)—CH₂—O—CH₃ H H—CO—CH₃ Cl H 1397 —CH(CH₃)—CH₂—O—CH₃ H H —OH H H 1398 —CH(CH₃)—CH₂—O—CH₃H H —OH —OCH₃ H 1399 —CH(CH₃)—CH₂—O—CH₃ H H —OCH₃ H —OCH₃ 1400—CH(CH₃)—CH₂—O—CH₃ H H —SCH₃ H H 1401 —CH(CH₃)—CH₂—O—CH₃ H H —OCH₃ H H1402 —CH(CH₃)—CH₂—O—CH₃ H H —OCH₃ —OCH₃ —OCH₃ 1403 —CH(CH₃)—CH₂—O—CH₃ HH —OH —OCH₃ —OCH₃ 1404 —CH(CH₃)—CH₂—O—CH₃ H H H —SCH₃ H 1405—CH(CH₃)—CH₂—O—CH₃ H H H —OCH₃ H 1406 —CH(CH₃)—CH₂—O—CH₃ H H —OCH₃ —OH H1407 —CH(CH₃)—CH₂—O—CH₃ H —OCH₃ —CH₃ H H 1408 —CH(CH₃)—CH₂—O—CH₃ H H—CH₂—CH₃ H H 1409 —CH(CH₃)—CH₂—O—CH₃ H —OCH₃ —CH(CH₃)₂ H H 1410—CH(CH₃)—CH₂—O—CH₃ H H —C₃H₇-n H H 1411 —CH(CH₃)—CH₂—O—CH₃ H H —OCH₂—CH₃H H 1412 —CH(CH₃)—CH₂—O—CH₃ H H F H H 1413 —CH(CH₃)—CH₂—O—CH₃ H H Cl H H1414 —CH(CH₃)—CH₂—O—CH₃ H H Br H H 1415 —CH(CH₃)—CH₂—O—CH₃ H H Cl Cl H1416 —CH(CH₃)—CH₂—O—CH₃ H H OH OH OH 1417 —CH(CH₃)—CH₂—O—CH₃ H Cl Cl HCl 1418 —CH(CH₃)—CH₂—O—CH₃ H H —CF₃ H H 1419 —CH(CH₃)—CH₂—O—CH₃ H H—OCF₃ H H 1420 —CH(CH₃)—CH₂—O—CH₃ H H —C₂F₅ H H 1421 —CH(CH₃)—CH₂—O—CH₃H H —C₄H₉-tert H H 1422 —CH(CH₃)—CH₂—O—CH₃ H H —OC₃H₇-i H H 1423—CH(CH₃)—CH₂—O—CH₃ H H —SO—CH₃ H H 1424 —CH(CH₃)—CH₂—O—CH₃ H H —SO₂—CH₃H H 1425 —CH(CH₃)—CH₂—O—CH₃ H H —NH—CH₂—CH₃ H H 1426 —CH(CH₃)—CH₂—O—CH₃H H —O—CH₂—CH═CH₂ H H 1427 —CH(CH₃)—CH₂—O—CH₃ H H —O—CH₂—C═CH H H 1428—CH(CH₃)—CH₂—O—CH₃ H H —NH—CH₂—CH₂—NH—CH₃ H H 1429 —CH(CH₃)—CH₂—O—CH₃ HH —SO₂—C₂H₅ H H 1430 —CH(CH₃)—CH₂—O—CH₃ H H —SO₂—CH₃ Cl H 1431—CH(CH₃)—CH₂—O—CH₃ H H —CH₂—CN H H 1432 —CH(CH₃)—CH₂—O—CH₃ H H—CH—(CH₃)—CN H H 1433 —CH(CH₃)—CH₂—O—CH₃ H H —C(CH₃)₂—CN H H 1434—CH(CH₃)—CH₂—O—CH₃ H H —CH—(C₂H₅)—CN H H 1435 —CH(CH₃)—CH₂—O—CH₃ H H—C(C₂H₅)₂—CN H H 1436 —CH(CH₃)—CH₂—O—CH₃ H H —CH₂—CH₂—CN H H 1437—CH(CH₃)—CH₂—O—CH₃ H H —CH(CH₃)—CH₂—CN H H 1438 —CH(CH₃)—CH₂—O—CH₃ H H—CH₂—CO₂—CH₃ H H 1439 —CH(CH₃)—CH₂—O—CH₃ H H —CH(CH₃)—CO₂—CH₃ H H 1440—CH₂—CH₂—O—CH₂—CH₂— H —CH₂—O—CH₃ H H 1441 —CH₂—CH₂—O—CH₂—CH₂— H—NH—CO—CH₃ H H 1443 —CH₂—CH₂—O—CH₂—CH₂— H —CH₂—NH—CO—CH₃ H H 1444—CH₂—CH₂—O—CH₂—CH₂— H —CH(CH₃)—NH—CO—CH₃ H H 1445 —CH₂—CH₂—O—CH₂—CH₂— H—C(CH₃)₂—NH—CO—CH₃ H H 1446 —CH₂—CH₂—O—CH₂—CH₂— H —CH(CH₃)—O—CH₃ H H1447 —CH₂—CH₂—O—CH₂—CH₂— H —C(CH₃)₂—O—CH₃ H H 1448 —CH₂—CH₂—O—CH₂—CH₂— H—CH(CH₃)—O—CO—CH₃ H H 1449 —CH₂—CH₂—O—CH₂—CH₂— H —CH₂—O—CO—CH₃ H H 1450—CH₂—CH₂—O—CH₂—CH₂— H —C(CH₃)₂—O—CO—CH₃ H H 1451 —CH₂—CH₂—O—CH₂—CH₂— H—CH₂—CH₂—O—H H H 1452 —CH₂—CH₂—O—CH₂—CH₂— H —CH₂—CH₂—O—CH₃ H H 1453—CH₂—CH₂—O—CH₂—CH₂— H

H H 1454 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1455 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1456 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1457 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1458 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1459 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1460 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1461 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1462 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1463 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1464 —CH₂—CH₂—O—CH₂—CH₂— H

H H 1465 —CH₂—CH₂—O—CH₂—CH₂— H H H H 1466 —CH₂—CH₂—O—CH₂—CH₂— H CN H H1467 —CH₂—CH₂—O—CH₂—CH₂— H —C(CH₃)₂—OH H H 1468 —CH₂—CH₂—O—CH₂—CH₂— H—CH₂—OH H H 1469 —CH₂—CH₂—O—CH₂—CH₂— H —CO—CH₃ H H 1470—CH₂—CH₂—O—CH₂—CH₂— H —C(═NOH)—CH₃ H H 1471 —CH₂—CH₂—O—CH₂—CH₂— H—CH(OH)—CH₃ H H 1472 —CH₂—CH₂—O—CH₂—CH₂— H (3) —CO—O—CH₂— (4) H 1473—CH₂—CH₂—O—CH₂—CH₂— H —CH₂—O—CO—CH₃ H H 1474 —CH₂—CH₂—O—CH₂—CH₂— H—C(═NO—CH₃)—CH₃ H H 1475 —CH₂—CH₂—O—CH₂—CH₂— H —CO—O—CH₃ H H 1476—CH₂—CH₂—O—CH₂—CH₂— H —NH—CO—C₃H₅-cycl. H H 1477 —CH₂—CH₂—O—CH₂—CH₂— H—CO—CH₃ Cl H 1478 —CH₂—CH₂—O—CH₂—CH₂— H —OH H H 1479 —CH₂—CH₂—O—CH₂—CH₂—H —OH —OCH₃ H 1480 —CH₂—CH₂—O—CH₂—CH₂— H —OCH₃ H —OCH₃ 1481—CH₂—CH₂—O—CH₂—CH₂— H —SCH₃ H H 1482 —CH₂—CH₂—O—CH₂—CH₂— H —OCH₃ H H1483 —CH₂—CH₂—O—CH₂—CH₂— H —OCH₃ —OCH₃ —OCH₃ 1484 —CH₂—CH₂—O—CH₂—CH₂— H—OH —OCH₃ —OCH₃ 1485 —CH₂—CH₂—O—CH₂—CH₂— H H —SCH₃ H 1486—CH₂—CH₂—O—CH₂—CH₂— H H —OCH₃ H 1487 —CH₂—CH₂—O—CH₂—CH₂— H —OCH₃ —OH H1488 —CH₂—CH₂—O—CH₂—CH₂— —OCH₃ —CH₃ H H 1489 —CH₂—CH₂—O—CH₂—CH₂— H—CH₂—CH₃ H H 1490 —CH₂—CH₂—O—CH₂—CH₂— —OCH₃ —CH(CH₃)₂ H H 1491—CH₂—CH₂—O—CH₂—CH₂— H —C₃H₇-n H H 1492 —CH₂—CH₂—O—CH₂—CH₂— H —OCH₂—CH₃ HH 1493 —CH₂—CH₂—O—CH₂—CH₂— H F H H 1494 —CH₂—CH₂—O—CH₂—CH₂— H Cl H H1495 —CH₂—CH₂—O—CH₂—CH₂— H Br H H 1496 —CH₂—CH₂—O—CH₂—CH₂— H Cl Cl H1497 —CH₂—CH₂—O—CH₂—CH₂— H OH OH OH 1498 —CH₂—CH₂—O—CH₂—CH₂— Cl Cl H Cl1499 —CH₂—CH₂—O—CH₂—CH₂— H —CF₃ H H 1500 —CH₂—CH₂—O—CH₂—CH₂— H —OCF₃ H H1501 —CH₂—CH₂—O—CH₂—CH₂— H —C₂F₅ H H 1502 —CH₂—CH₂—O—CH₂—CH₂— H—C₄H₉-tert H H 1503 —CH₂—CH₂—O—CH₂—CH₂— H —OC₃H₇-i H H 1504—CH₂—CH₂—O—CH₂—CH₂— H —SO—CH₃ H H 1505 —CH₂—CH₂—O—CH₂—CH₂— H —SO₂—CH₃ HH 1506 —CH₂—CH₂—O—CH₂—CH₂— H —NH—CH₂—CH₃ H H 1507 —CH₂—CH₂—O—CH₂—CH₂— H—O—CH₂—CH═CH₂ H H 1508 —CH₂—CH₂—O—CH₂—CH₂— H —O—CH₂—C═CH H H 1509—CH₂—CH₂—O—CH₂—CH₂— H —NH—CH₂—CH₂—NH—CH₃ H H 1510 —CH₂—CH₂—O—CH₂—CH₂— H—SO₂—C₂H₅ H H 1511 —CH₂—CH₂—O—CH₂—CH₂— H —SO₂—CH₃ Cl H 1512—CH₂—CH₂—O—CH₂—CH₂— H —CH₂—CN H H 1513 —CH₂—CH₂—O—CH₂—CH₂— H—CH—(CH₃)—CN H H 1514 —CH₂—CH₂—O—CH₂—CH₂— H —C(CH₃)₂—CN H H 1515—CH₂—CH₂—O—CH₂—CH₂— H —CH—(C₂H₅)—CN H H 1516 —CH₂—CH₂—O—CH₂—CH₂— H—C(C₂H₅)₂—CN H H 1517 —CH₂—CH₂—O—CH₂—CH₂— H —CH₂—CH₂—CN H H 1518—CH₂—CH₂—O—CH₂—CH₂— H —CH(CH₃)—CH₂—CN H H 1519 —CH₂—CH₂—O—CH₂—CH₂— H—CH₂—CO₂—CH₃ H H 1520 —CH₂—CH₂—O—CH₂—CH₂— H —CH(CH₃)—CO₂—CH₃ H H 1521—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—O—CH₃ H H 1522 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H —NH—CO—CH₃ H H 1523 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—NH—CO—CH₃ H H 1524—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH(CH₃)—NH—CO—CH₃ H H 1525—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(CH₃)₂—NH—CO—CH₃ H H 1526—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH(CH₃)—O—CH₃ H H 1527—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(CH₃)₂—O—CH₃ H H 1528—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH(CH₃)—O—CO—CH₃ H H 1529—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—O—CO—CH₃ H H 1530—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(CH₃)₂—O—CO—CH₃ H H 1531—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CH₂—O—H H H 1532—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CH₂—O—CH₃ H H 1533—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1534 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1535 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1536 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1537 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1538 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1539 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1540 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1541 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1543 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1544 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1545 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H

H H 1546 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H H H H 1547 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H CN H H 1548 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(CH₃)₂—OH H H 1549—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—OH H H 1550 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—CO—CH₃ H H 1551 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(═NOH)—CH₃ H H 1552—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH(OH)—CH₃ H H 1553 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H (3) —CO—O—CH₂— (4) H 1554 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—O—CO—CH₃ H H1555 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(═NO—CH₃)—CH₃ H H 1556—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CO—O—CH₃ H H 1557 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—NH—CO—C₃H₅-cycl. H H 1558 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CO—CH₃ Cl H 1559—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OH H H 1560 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OH—OCH₃ H 1561 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OCH₃ H —OCH₃ 1562—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —SCH₃ H H 1563 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—OCH₃ H H 1564 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OCH₃ —OCH₃ —OCH₃ 1565—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OH —OCH₃ —OCH₃ 1566 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H H —SCH₃ H 1567 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H H —OCH₃ H 1568—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —OCH₃ —OH H 1569 —CH₂—CH₂—N(CH₃)—CH₂—CH₂——OCH₃ —CH₃ H H 1570 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CH₃ H H 1571—CH₂—CH₂—N(CH₃)—CH₂—CH₂— —OCH₃ —CH(CH₃)₂ H H 1572—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C₃H₇-n H H 1573 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—OCH₂—CH₃ H H 1574 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H F H H 1575—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H Cl H H 1576 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H Br H H1577 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H Cl Cl H 1578 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— HOH OH OH 1579 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— Cl Cl H Cl 1580—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CF₃ H H 1581 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—OCF₃ H H 1582 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C₂F₅ H H 1583—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C₄H₉-tert H H 1584 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H —OC₃H₇-i H H 1585 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —SO—CH₃ H H 1586—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —SO₂—CH₃ H H 1587 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—NH—CH₂—CH₃ H H 1588 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —O—CH₂—CH═CH₂ H H 1589—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —O—CH₂—C═CH H H 1590 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H —NH—CH₂—CH₂—NH—CH₃ H H 1591 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —SO₂—C₂H₅ H H1592 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —SO₂—CH₃ Cl H 1593—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CN H H 1594 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H—CH—(CH₃)—CN H H 1595 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(CH₃)₂—CN H H 1596—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH—(C₂H₅)—CN H H 1597—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —C(C₂H₅)₂—CN H H 1598—CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CH₂—CN H H 1599 —CH₂—CH₂—N(CH₃)—CH₂—CH₂—H —CH(CH₃)—CH₂—CN H H 1600 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH₂—CO₂—CH₃ H H1601 —CH₂—CH₂—N(CH₃)—CH₂—CH₂— H —CH(CH₃)—CO₂—CH₃ H H

For the following example compounds physico-chemical data have beenobtained and are displayed in order to illustrate the working of thepresent invention, including the outlined methods of synthesis. Thenumber of given data may not be interpreted as a limitation of theinvention. TABLE B Comp. Melting point [OC] or No. 1H-NMR [δ in ppm]01.0025 244-245 01.0026 260-261 01.0027 219-220 01.0028 214-215 01.0029228-229 01.0030 >260 01.0031 216-217 01.0032 >260 01.0034 237-23801.0035 223-225 01.0038 133-234 01.0039 244-245 01.0042 115-117 01.0052243-245 01.0169 244-245 01.0307 >260 01.0315 235-236 01.0377 >26001.0448 188-189 01.0588 255-256 01.0658 206-207 01.0729 >260 01.0869196-197 01.0940 230 01.1013 >260 01.1083 178-179 01.1465 233-234 01.1546239-240 02.0026 236-238 02.0027 252-253 02.0028 >260 02.0031 260-26102.0038 256-258 02.0041 238-240 02.0042 223-225 02.0052 208-21002.0054 >260 02.0058 >260 02.0059 >260 02.0061 239-240 02.0063 222-22302.0123 >260 02.0124 >260 02.0193 >260 02.1130 259-260 03.0025 >26003.0026 >260 03.0029 255-256 03.0035 241.242 03.0236 224.227 03.024288-91 04.0035 236-237 06.0025 >260 06.0026 >260 06.0029 >260 06.0035249-250 07.0025 212-213 07.0026 234-235 07.0029 198-200 10.0029 228-22910.0518 90-92In the following, examples of test systems in plant protection areprovided which can demonstrate the efficiency of the compounds of theformula I (designated as ,,active ingredient “or ,,test compounds”):

Biological Examples Example B-1 Effect Against Puccinia graminis onWheat (Brownrust on Wheat)

a) Residual Protective Activity

1 week old wheat plants cv. Arina are treated with the formulatedtest-compound (0.02% active substance) in a spray chamber. Two daysafter application wheat plants are inoculated by spraying a sporesuspension (1×10⁵ ureidospores/ml) on the test plants. After anincubation period of 1 day at +20° C. and 95% relative atmospherichumidity (r. h.) plants are kept for 9 days at +20° C. and 60% r.h. in agreenhouse. The disease incidence is assessed 10 days after inoculation.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

b) Systemic Activity

An aqueous spray liquor prepared from the formulated test compound(0.002% active substance, based on the volume of soil) is poured ontowheat plants 5 days after sowing. Care is taken that the spray liquordoes not come into contact with the above-ground parts of the plant. 48hours later, the plants are inoculated with a spore suspension of thefungus. After an incubation period of 48 hours (95 to 100% r.h. at +20°C.), the plants are placed in a greenhouse at +20° C. 12 days afterinfection, the disease incidence is evaluated.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

Example B-2 Effect Against Phytophthora infestans on Tomatoes (LateBlight on Potato)

a) Residual Protective Activity

3 week old tomato plants cv. Roter Gnom are treated with the formulatedtest compound (0.02% active substance) in a spray chamber. Two day afterapplication the plants are inoculated by spraying a sporangia suspension(2×10⁴ sporangia/ml) on the test plants. After an incubation period of 4days at +18° C. and 95% r.h. in a growth chamber the disease incidenceis assessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compounds 01.0025, 01.0028, 01.0031,01.0307, 01.0315, 01.0729, 02.0027, 02.0028, 02.0031, 02.0038, 10.0029,and 10.0518 exhibited over 70% control of the fungal infection in thistest.

b) Systemic Activity

An aqueous suspension prepared from the formulated test compound (0.002%active substance, based on the volume of soil) is poured onto tomatoplants which have been cultivated for three weeks. Care is taken thatthe spray liquor does not come into contact with the above-ground partsof the plant. 48 hours later, the plants are inoculated with a sporangiasuspension of the fungus. Evaluation of the disease incidence takesplace 5 days after infection, during which period conditions of 90 to100% r.h. and +20° C. are maintained.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compounds 01.0025, 01.0028, 01.0031,01.0307, 01.0315, 01.0729, 02.0027, 02.0028, 02.0031, 02.0038, 10.0029,and 10.0518 exhibited over 70% control of the fungal infection in thistest.

Example B-3 Effect Against Phytophthora infestans/Potato (Late Blight onPotato)

5 week old potato plants cv. Bintje are treated with the formulated testcompound (0.02% active substance) in a spray chamber. Two days afterapplication the plants are inoculated by spraying a sporangia suspension(1.4×10⁵ sporangia/ml) on the test plants. After an incubation period of4 days at +18° C. and 95% r. h. in a growth chamber the diseaseincidence is assessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compounds 01.0025, 01.0028, 01.0031,01.0307, 01.0315, 01.0729, 02.0027, 02.0028, 02.0031, 02.0038, 10.0029,and 10.0518 exhibited over 70% control of the fungal infection in thistest.

Example B-4 Effect Against Plasmopara viticola on Grapevine (Grape DownyMildew)

5 week old grape seedlings cv. Gutedel are treated with the formulatedtest compound (0.02% active substance) in a spray chamber. One day afterapplication grape plants are inoculated by spraying a sporangiasuspension (4×10⁴ sporangia/ml) on the lower leaf side of the testplants. After an incubation period of 6 days at +22° C. and 95% r. h. ina greenhouse the disease incidence is assessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compounds 01.0025, 01.0027, 01.0028,01.0030, 01.0031, 01.0034, 01.0042, 01.0169, 01.0658, 01.0729, 01.0869,02.0027, 02.0028, 02.0031, 02.0038, 10.0029 and 10.0518 exhibited over70% control of the fungal infection in this test.

Example B-5 Residual Protective Activity Against Venturia inaequalis onApples (Scab on Apple)

4 week old apple seedlings cv. McIntosh are treated with the formulatedtest compound (0.02% active substance) in a spray chamber. One day afterapplication apple plants are inoculated by spraying a spore suspension(4×10⁵ conidia/ml) on the test plants. After an incubation period of 4days at +21° C. and 95% r. h. the plants are placed for 4 days at +21°C. and 60% r. h. in a greenhouse. After another 4 day incubation periodat +21° C. and 95% r. h. the disease incidence is assessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

Example B-6 Effect Against Erysiphe graminis on Barley (Powdery Mildewon Barley)

a) Residual Protective Activity

Barley plants of approximately 8 cm height are sprayed to drip pointwith an aqueous spray liquor prepared from wettable powder of the activeingredient (0.02% active substance), and dusted 3 to 4 hours later withconidia of the fungus. The infected plants are placed in a greenhouse at+22° C. 12 days after infection, the fungal attack is evaluated.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

b) Systemic Activity

An aqueous spray liquor prepared from the formulated test compound(0.002% active substance, based on the volume of soil) is poured ontobarley plants of approximately 8 cm height. Care is taken that the sprayliquor does not come into contact with the above-ground parts of theplant. 48 hours later, the plants are dusted with conidia of the fungus.The infected plants are placed in a greenhouse at +22° C. 12 days afterinfection, the disease incidence is evaluated.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

Example B-7 Botrytis cinerea/Grape (botrytis on Grapes)

5 week old grape seedlings cv. Gutedel are treated with the formulatedtest compound (0.02% active substance) in a spray chamber. Two daysafter application grape plants are inoculated by spraying a sporesuspension (1×10⁶ conidia/ml) on the test plants. After an incubationperiod of 4 days at +21° C. and 95% r. h. in a greenhouse the diseaseincidence is assessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compound 01.0042 exhibited over 70%control of the fungal infection in this test.

Example B-8 Effect Against Botrytis cinerea/Tomato (botrytis onTomatoes)

4 week old tomato plants cv. Roter Gnom are treated with the formulatedtest compound 0.02% active substance) in a spray chamber. Two days afterapplication tomato plants are inoculated by spraying a spore suspension(1×10⁵ conidia/ml) on the test plants. After an incubation period of 4days at +20° C. and 95% r. h. in a greenhouse the disease incidence isassessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compound 01.0042 exhibited over 70%control of the fungal infection in this test.

Example B-9 Effect Against Pyricularia oryzae/Rice (Rice Blast)

3 week old rice plants cv. Sasanishiki are treated with the formulatedtest compound (0.02% active substance) in a spray chamber. Two daysafter application rice plants are inoculated by spraying a sporesuspension (1×10⁵ conidia/ml) on the test plants. After an incubationperiod of 6 days at +25° C. and 95% r. h. the disease incidence isassessed.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

Example B-10 Effect Against Pyrenophora teres (Helminthosporium)/Barley(Net Blotch on Barley)

1 week old barley plants cv. Regina are treated with a formulated testcompound (0.02% active substance) in a spray chamber. Two days afterapplication barley plants are inoculated by spraying a spore suspension(3×10⁴ conidia/ml) on the test plants. After an incubation period of 2days at +20° C. and 95% r.h. plants are kept for 2 days at +20° C. and60% r.h. in a greenhouse. The disease incidence is assessed 4 days afterinoculation.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

At the indicated concentration compound 01.0028 exhibited over 70%control of the fungal infection in this test.

Example B-11 Effect Against Fusarium culmorum/Wheat (Fusarium HeadBlight on Wheat)

A conidia suspension of F. culmorum (7×10⁵ conidia/ml) is mixed with theformulated test compound (0.002% active substance).. The mixture isapplied into a pouch which has been equipped before with a filter paper.After the application wheat seeds (cv. Orestis) are sown into the upperfault of the filter paper. The prepared pouches are then incubated for11 days at approx. +10° C. to +18° C. and a relative humidity of 100%with a light period of 14 hours. The evaluation is made by assessing thedegree of disease occurrence in the form of brown lesions on the roots.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

Example B-12 Effect Against Septoria nodorum/Wheat (Septoria Leaf Spoton Wheat)

1 week old wheat plants cv. Arina are treated with a formulated testcompound (0.02% active substance) in a spray chamber. One day afterapplication wheat plants are inoculated by spraying a spore suspension(5×10⁵ conidia/ml) on the test plants. After an incubation period of 1day at +20° C. and 95% r.h. plants are kept for 10 days at +20° C. and60% r.h. in a greenhouse. The disease incidence is assessed 11 daysafter inoculation.

Compounds of Tables 1 to 10 Show Good Activity in this Test.

1. A N-[2-amino-thiazol-5-yl-pyrimidin-yl]-N-phenyl-amine of the formulaI

wherein R₁ is hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₃-C₇cycloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl, C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl,C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl,C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, aryl-C₁-C₄alkyl, heteroaryl-C₁-C₄alkyl,or a group —CO—R₉, —CO—OR₁₀, —CO—NR₁₀R₁₁, or —NR₁₀R₁₁; R₂ is hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl,C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl or a group —CO—R₉; R₁ and R₂together with the nitrogen to which they are bound form an optionallysubstituted N-linked saturated or unsaturated N-ring system which maycontain oxygen or sulfur as a ring member, or form a group—N═CR₉—NR₁₀R₁₁; R₃ is hydrogen, halogen or C₁-C₄alkyl; R₄ is hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆cyanoalkyl, C₃-C₇cycloalkyl,C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, amino,C₁-C₆alkylamino, di(C₁-C₄alkyl)-amino, halogen, hydroxy, mercapto,cyano, C₁-C₆alkoxy, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆haloalkoxy,C₁-C₈alkanoyloxy-C₁-C₆alkyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆hydroxyalkyl, C₁-C₄alkoxy-C₁-C₆alkyl,C₁-C₆aminoalkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, C₁-C₈alkoxycarbonyl,C₁-C₈alkanoyl-C₁-C₆aminoalkyl, optionally substituted heterocyclyl,optionally substituted aryl, optionally substituted heteroaryl, or agroup —CO—R₉, —O—CO—R₉, —NH—CO—R₉, —(C₁-C₆alkylene-)-CO—R₉,—C(—O—C₁-C₆alkylene-O—)-R₉, —C(═NOR₈)—R₉ or —CO—NR₁₀R₁₁; R₅ is hydrogen,hydroxy, halogen, C₁-C₆alkyl, C₁-C₆alkoxy or C₁-C₆haloalkyl; R₆ ishydrogen, C₁-C₆alkyl or C₁-C₆haloalkyl; R₇ is thienyl , pyridinyl oraryl each optionally substituted with one to three substituentsindependently selected from the group comprising halogen, C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy; R₈ is hydrogen,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxy-C₁-C₆alkyl, or agroup —CO—R₉ or —CO—OR₁₀; R₉ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl, aryl,C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl, aryl-C₁-C₄alkyl, heteroaryl orheteroaryl-C₁-C₄alkyl; R₁₀ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl or C₁-C₄alkoxy-C₁-C₆alkyl; R₁₁ is C₁-C₆alkyl,C₃-C₇cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₆alkyl,aryl or heteroaryl; or a salt thereof.
 2. A compound according to claim1, wherein R₃, R₆ and R₈ are all hydrogen.
 3. A compound according toclaim 1, wherein R₁ is hydrogen, C₁-C₄alkyl, or is a group —CO—R₉; andR₂ is hydrogen or C₁-C₄alkyl; or R₁ and R₂ together form the group—N═CR₉—NR₁₀R₁₁; R₃ is hydrogen or methyl; and R₄ is hydrogen, hydroxy,amino, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄cyanoalkyl, C₁-C₆alkylamino,di(C₁-C₄alkyl)-amino, C₁-C₆aminoalkyl, halogen, mercapto, cyano,C₁-C₆alkoxy, C₂-C₆alkenyloxy, C₂-C₆alkynyloxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆hydroxyalkyl,C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₄alkyl-C₁-C₆aminoalkyl,di(C₁-C₄alkyl)-C₁-C₆aminoalkyl, C₁-C₄alkoxycarbonyl; —CO—R₉, or—NH—CO—R₉; and R₅ is hydrogen, hydroxy, methoxy or methylthio; and R₆ ishydrogen or methoxy; and R₇ is 4-pyridyl or optionally substituted arylcarrying one to three substituents independently selected from the groupcomprising halogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl andC₁-C₄haloalkoxy; and R₈ is hydrogen, C₁-C₄alkanoyl, C₁-C₄haloalkanoyl orC₁-C₄alkyl.
 4. A compound according to claim 1, wherein; R₁ is hydrogen,methyl, trifluoroacetyl, pentafluoropropionyl or heptafluorobutyryl; andR₂ is hydrogen or C₁-C₄alkyl; or R₁ and R₂ are both hydrogen or R₁ andR₂ together form the groups —N═CH—N(CH₃)₂ or —N═C(CH₃)—N(CH₃)₂; and R₃is hydrogen or methyl; and R₄ is hydrogen, hydroxy, C₁-C₄alkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄haloalkyl, C₁-C₄cyanoalkyl,C₁-C₄alkanoyloxy, C₁-C₄hydroxyalkyl, C₁-C₄haloalkanoyloxy,C₁-C₄alkanoyl-C₁-C₆aminoalkyl, C₁-C₄alkanoyloxy-C₁-C₄alkyl,C₁-C₄alkanoyl, C₁-C₄alkylthio or C₁-C₄alkoxycarbonyl; and R₅ is hydrogenor hydroxy; and R₆ is hydrogen; and R₇ is phenyl or halophenyl; and R₈is hydrogen or C₁-C₄fluoroalkanoyl.
 5. A compound according to claim 1,wherein; R₁ is acetyl; and R₂ is hydrogen or methyl; or R₁ and R₂together form the groups —N=CH—N(CH₃)₂ or —N═C(CH₃)—N(CH₃)₂; and R₃ ishydrogen; and R₄ is hydrogen, hydroxy, cyano, fluorine, chlorine,bromine, methyl, tert.butyl, methylthio, trifluoromethyl, hydroxymethyl,cyanomthyl, 2-cyanoethyl, 1-hydroxyethyl, 2-hydroxyisopropyl, acetyl,2-hydroximino-ethyl, 2-methoximino-ethyl, acetoxymethyl,methoxycarbonyl, methoxy, ethoxy or trifluoromethoxy; and R₅ and R₆ arehydrogen; and R₇ is phenyl, 4-fluorophenyl or 4-chlorophenyl; and R₈ ishydrogen or C₁-C₄fluoroalkanoyl.
 6. A compound according to claim 1,wherein R₁, R₂, R₃, R₅, R₆ and R₈ are all hydrogen and R₄ is hydrogen,hydroxy, cyano, fluorine, chlorine, bromine, methyl, tert.butyl,methylthio, trifluoromethyl, cyanomethyl, 2-cyanoethyl, hydroxymethyl,1-hydroxyethyl, 2-hydroxyisopropyl, acetyl, 2-hydroximino-ethyl,2-methoximino-ethyl, acetoxymethyl, and R₇ is phenyl, 4-fluorophenyl or4-chlorophenyl.
 7. A compound according to claim 1, characterized bysubformula IA

wherein R₁ is hydrogen, C₁-C₄alkyl, or is a group —CO—R₉ or —CO—OR₁₀;and R₂ is hydrogen or C₁-C₄alkyl; or R₁ and R₂ together form the group—N═CR₉—NR₁₀R₁₁; and R₄ is hydrogen, cyano, hydroxy, C₁-C₄alkoxy,C₁-C₆aminoalkyl, C₁-C₈alkanoyloxy-C₁-C₄alkyl,C₁-C₈alkanoylamino-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆hydroxyalkylor C₁-C₄cyanoalkyl, and R₉ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄alkyl,C₁-C₄alkyl-C₃-C₇cycloalkyl-C₁-C₄alkyl, aryl, aryl-C₁-C₄alkyl, heteroarylor heteroaryl-C₁-C₄alkyl; R₁₀ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₇cycloalkyl-C₁-C₄alkyl or C₁-C₄alkoxy-C₁-C₆alkyl; and R₁₂ ishalogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy,and R₁₃ is C₁-C₄alkyl.
 8. A compound according to claim 1, characterizedby subformula IB

wherein R₄ is hydrogen, hydroxy, cyano, C₁-C₄alkoxy, C₁-C₆aminoalkyl,C₁-C₈alkanoyloxy-C₁-C₄alkyl, C₁-C₈alkanoylamino-C₁-C₄alkyl,C₁-C₄alkoxy-C₁-C₆alkyl, C₁-C₆hydroxyalkyl or C₁-C₄cyanoalkyl, and R₁₂ ishalogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄haloalkyl and C₁-C₄haloalkoxy. 9.A compound according to claim 1, selected from the group comprisingN-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine,N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxyethyl)-phenyl]-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxyethyl)-phenyl]-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;N-[4-(2-amino-4-phenyl,thiazol-5-yl)-pyrimidin-2-yl]-N-(3-acetyl-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetyl-phenyl)-amine;N-[4-(2-amino-4-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-(3-cyano-phenyl)-amine;{4-[2-acetylamino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetoxymethyl-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-methoxy-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(4-fluoro-phenyl)-amine;N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyano-phenyl)-amine;N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyanomethyl-phenyl)-amine;andN-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyanomethyl-phenyl)-amine.10. A process for the preparation of the compound according to claim 1,comprising a) reacting a compound of formula II

 wherein R₁, R₂ and R₇ are as defined for formula I and Y stands for aleaving group such as halogen, alkylthio, alkylsulfinyl, alkylsulfonyl,with an aniline of the formula

 wherein R₃, R₄, R₅, R₆ and R₈ are as defined for formula I, or b)reacting a compound of formula VIII

 wherein R₃, R₄, R₅, R₆, R₇ and R₈ are as defined for formula I and Z isa leaving group such as halogen, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl orC₁-C₄alkylsulfonyl with an amine of the formula HNR₁R₂.wherein R₁ and R₂are as defined for formula I in claim
 1. 11. A composition forcontrolling and protecting against phytopathogenic microorganisms,comprising a compound of formula I according to claim 1 as activeingredient together with a suitable carrier.
 12. The use of a compoundof formula I according to claim 1 in protecting plants againstinfestation by phytopathogenic microorganisms.
 13. A method ofcontrolling and preventing an infestation of crop plants byphytopathogenic microorganisms, which comprises the application of acompound of formula I according to claim 1 as active ingredient to theplant, to parts of plants or to the locus thereof.
 14. A methodaccording to claim 13, wherein the phytopathogenic microorganisms arefungal organisms.